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ETH Zurich - D-CHAB - LOC - Bode Research Group - Publications

Publications

(66)	Dumas, A. M., Molander, G. A., Bode, J. W. "Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water", Angew. Chem. Int. Ed. 2012, Early View. Link (DOI: 10.1002/anie.201201077)
(65)	Dumas, A. M.; Bode, J. W. "Synthesis of Acyltrifluoroborates" Org. Lett. 2012, 14, 2138–2141. Link
(64)	Lyngvi, E.; Bode, J. W.; Schoenebeck, F. "A Computational Study of the Origin of Stereoinduction in NHC-Catalyzed Annulation Reactions of alpha,beta-Unsaturated Acyl Azoliums", Chem. Sci. 2012, Accepted Manuscript. Link (DOI: 10.1039/C2SC20331F)
(63)	Larson, K. K.; He, M.; Teichert, J. F.; Naganawa, A.; Bode, J. W. "Chemical Sensing with Shapeshifting Organic Molecules", Chem. Sci. 2012, 3, 1825–1828. Link - highlighted in Nature Chem. 2012, 4, 336–337. Link
(62)	Pattabiraman, V. R.; Ogunkoya, A. O.; Bode, J. W. "Chemical Protein Synthesis by Chemoselective α-Ketoacid–Hydroxylamine (KAHA) Ligations with 5-Oxaproline" Angew. Chem. Int. Ed. 2012, Early View. Link (DOI: 10.1002/anie.201200907) - selected as a Hot Paper & Cover. Link
(61)	Gerfaud, T.; Chiang, Y.-L.; Kreituss, I.; Russak, J.; Bode, J. W.; "Enantioselective, chromatography-free synthesis of β3-amino acids with natural and unnatural side chains", Org. Process Res. Dev. 2012, 16, 687–696. Link
(60)	Fukuzumi, T.; Ju, L.; Bode, J. W. "Chemoselective Cyclization of Unprotected Linear Peptides by alpha-Ketoacid–Hydroxyamine Amide-Ligation", Org. Biomol. Chem. 2012, Accepted Manuscript. Link (DOI: 10.1039/C2OB25129A) - This article is part of the collection: Organic & Biomolecular Chemistry 10th Anniversary.
(59)	Book chapter: Chiang, P.-C.; Bode, J. W. "N-Heterocyclic Carbene Catalyzed Reactions of alpha-Functionalized Aldehydes", Science of Synthesis: Asymmetric Organocatalysis, Vol. 1, 2012, Georg Thieme Verlag, 639–672 [Ed: B. List]
(58)	Mahatthananchai, J.; Kaeobamrung, J.; Bode, J. W. ACS Catal. 2012, 2, 494–503. (Special issue on catalysis at ETH Zürich) Link
(57)	Pusterla, I.; Bode, J. W. "The Mechanism of the α-Ketoacid–Hydroxylamine (KAHA) Amide-Forming Ligation", Angew. Chem. Int. Ed. 2012, 51, 513–516. Link
(56)	Mahatthananchai, J.; Bode, J. W. "The effect of the N-mesityl group in NHC-catalyzed reactions", Chem. Sci. 2012, 3, 192–197. Link
(55)	Huang, Y.-L.; Frey, R; Juarez-Garcia, M. E.; Bode, J. W. "Synthesis of Aza-Surfactin and 3-Epi-aza-surfactin" Heterocycles 2012, 84, 1179–1191. Link
(54)	Review article: Pattabiraman, V.; Bode, J. W. “Rethinking Amide Bond Synthesis”, Nature 2011, 480, 471–479. Link
(53)	Binanzer, M.; Hsieh S.-Y.; Bode, J. W. "Catalytic Kinetic Resolution of Cyclic Secondary Amines", J. Am. Chem. Soc. 2011, 133, 19698–19701. Link -reviewed in Synfacts 2012, 8, 211. Link
(52)	Wanner, B.; Mahatthananchai, J.; Bode, J. W. "Enantioselective Synthesis of Dihydropyridinones via NHC-Catalyzed Aza-Claisen Reaction," Org. Lett. 2011, 13, 5378–5381. Link
(51)	Schäfer, G.; Bode, J. W. "Friedel-Crafts Benzylation of Activated and Deactivated Arenes", Angew. Chem. Int. Ed. 2011, 50, 10913–10916 Link - reviewed in Synfacts 2012, 8, 194. Link - highlighted in Org. Process Res. Dev. 2012. Link
(50)	He, M.; Bode, J. W. "Racemization as a stereochemical measure of dynamics and robustness in shape-shifting organic molecules", Proc. Nat. Acad. Sci. U.S.A. 2011, 36, 14752–14756. Link
(49)	Wu, J.; J. Ruiz-Rodríguez; Comstock, J. M.; Dong, J. Z.; Bode, J. W. "Synthesis of human GLP-1 (7–36) by chemoselective α-ketoacid–hydroxylamine peptide ligation of unprotected fragments", Chem. Sci. 2011, 2, 1976–1979. Link
(48)	Vo, C.-V; Mitchell, T. A.; Bode, J. W. "Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals", J. Am. Chem. Soc. 2011, 133, 14082–14089. Link - highlighted in Organic Chemistry Portal. Link
(47)	Perspective: Bode, J. W. "Organic Synthesis without Stoichiometric Reagents: A Guiding Principle for Reaction Development", Chimia 2011, 65, 150–156. Link
(46)	Review article: Chiang, P.-C.; Bode, J. W. "N-Mesityl Substituted Chiral Triazolium Salts: Opening a New World of N-Heterocyclic Carbene Catalysis", TCI MAIL 2011, 149, 2–17. Link
(45)	Chiang, P.-C.; Bode, J. W. "On the Role of CO₂ in NHC-Catalyzed Oxidation of Aldehydes", Org. Lett. 2011, 13, 2422–2425. Link
(44)	Mahatthananchai, J.; Zheng, P.; Bode, J. W. "α,β-Unsaturated Acyl Azoliums from N-Heterocyclic Carbene Catalyzed Reactions: Observation and Mechanistic Investigation", Angew. Chem. Int. Ed. 2011, 50, 1673–1677. Link
(43)	Zheng, P.; Gondo, C. A.; Bode, J. W. "Late-Stage Diversification of Chiral N-Heterocyclic-Carbene Precatalysts for Enantioselectvie Homoenolate Additions", Chem. Asian J. 2011, 6, 614–620. Link
(42)	Book chapter: Hackenberger, C. P. R.; Bode, J. W.; Schwarzer, D. "Chemoselective Peptide Ligation: A Privileged Tool for Protein Synthesis", Amino Acids, Peptides and Proteins in Organic Chemistry: Building Blocks, Catalysis and Coupling Chemistry, Volume 3 (ed A. B. Hughes), 2011. Link
(41)	Review article: Chiang, P.-C.; Bode, J. W. "N-Heterocyclic Carbenes as Organic Catalysts" in N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools; Díez-González, S., Ed.; RSC Catalysis Series No. 6; Royal Society of Chemistry: Cambridge, 2011; pp 399–435. Link (DOI: 10.1039/9781849732161-00399)
(40)	Lippert, A. R.; Naganawa, A.; Keleshian, V. L.; Bode, J. W. "Synthesis of Phototrappable Shape-Shifting Molecules for Adaptive Guest Binding" J. Am. Chem. Soc. 2010, 132, 15790–15799. Link
(39)	Narumi, T.; Bode, J. W. "α,α-Dicholoroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids", Heterocycles 2011, 82, 1515–1525. Link
(38)	Kaeobamrung, J.; Kozlowski. M. C.; Bode, J. W. "Chiral N-Heterocyclic Carbene-Catalyzed Generation of Ester Enolate Equivalents from α,β-Unsaturated Aldehydes for Enantioselective Diels–Alder Reactions", Proc. Nat. Acad. Sci. U.S.A. 2010, 107, 20661–20665. Link
(37)	Yu, S.; Ishida, H.; Juarez-Garcia, M. E.; Bode, J. W. "Unified synthesis of enantiopure β2h, β3h and β2,3-amino acids", Chem. Sci. 2010, 637–641. Link
(36)	Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. "An Enantioselective Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes", J. Am. Chem. Soc. 2010, 132, 8810–8812. Link -reviewed in Synfacts 2010, issue 09, 1071. Link
(35)	Struble, J. R.; Bode, J. W. "Synthesis of N-Mesityl Substituted Aminoindalnol-Derived Triazolium Salt [(5aS,10bR)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride]", Org. Synth. 2010, 87, 362–376. Link
(34)	Ju, L.; Bode, J. W. "Amide Formation by Decarboxylative Condensation of Hydroxyamines and α-Ketoacids: N-[(1S)-1-Phenylethyl]-benzeneacetamide", Org. Synth. 2010, 87, 218–225. Link
(33)	Juarez-Garcia, M. E.; Yu, S.; Bode, J. W. "Asymmetric Synthesis of Enantiopure Isoxazolidinone Monomers for the Synthesis of β3-Oligopeptides by Chemoselective Amide Ligation", Tetrahedron 2010, 66, 4841–4853. Link
(32)	Medina, S. I.; Wu, J.; Bode, J. W. "Nitrone Protecting Groups for Enantiopure N-Hydroxyamino Acids: Synthesis of N-Terminal Peptide Hydroxylamines for Chemoselective Ligations", Org. Biomol. Chem. 2010, 8, 3405–3417. Link
(31)	Flores, M. A.; Bode, J. W. "Chemoselective Protection of α-Ketoacids by Direct Annulations with Oximes", Org. Lett. 2010, 12, 1924–1927. Link
(30)	Mitchell, T. A.; Bode, J. W. "Synthesis of Dialkyl Ethers from Organotrifluoroborates and Acetal", J. Am. Chem. Soc. 2009, 131,18057–18059. Link -reviewed in Synfacts 2010, issue 03, 335. Link
(29)	Chiang, P.-C.; Kim, Y.; Bode, J. W. "Catalytic Amide Formation with α'-Hydroxyenones as Acylating Reagents", Chem. Commun., 2009, 4566–4568. Link -reviewed in Synfacts 2009, issue 09, 1042. Link
(28)	Chiang, P.-C.; Rommel, M.; Bode, J. W. "α'-Hydroxyenones as Mechanistic Probes and Scope-Expanding Surrogates for α,β-Unsaturated Aldehydes in N-Heterocyclic Carbene-Catalyzed Reactions", J. Am. Chem. Soc. 2009, 131, 8714–8718. Link
(27)	Valenta, P.; Drucker, N. A.; Bode, J. W. and Walsh, P. J. "Simple One-pot Conversion of Aldehydes and Ketones to Enals", Org. Lett. 2009, 11, 2117–2119. Link
(26)	Fukuzumi, T.; Bode, J. W. "A Reagent for the Convenient, Solid-Phase Synthesis of N-Terminal Peptide Hydroxylamines for Chemoselective Ligations" J. Am. Chem. Soc. 2009, 131, 3864–3865. Link
(25)	Struble, J. R.; Bode, J. W. "Formal Synthesis of Salinosporamide A via NHC-catalyzed Intramolecular Lactonization", Tetrahedron, 2009, 65, 4957–4967. Link
(24)	Ishida, H.; Carrillo, N.; Bode, J. W. "Synthesis of an enantiopure isoxazolidine monomer for β3-aspartic acid in chemoselective β-oligopeptide synthesis" Tetrahedron Lett. 2009, 50, 3258–3260. Link
(23)	Ju, L.; Bode, J. W. "A general strategy for the preparation of C-terminal peptide a-ketoacids by solid phase peptide synthesis", Org. Biomol. Chem. 2009, 7, 2259–2264. Link
(22)	Lippert, A. R.; Keleshian, V. L.; Bode, J. W. "Dynamic supramolecular complexation by shapeshifting organic molecules" Org. Biomol. Chem. 2009, 7, 1529–1532. Link
(21)	Kaeobamrung, J.; Bode, J. W. "Stereodivergency of Triazolium and Imidazolium-Derived NHCs for Catalytic, Enantioselective Cyclopentane Synthesis" Org. Lett. 2009, 11, 677–680. Link
(20)	Rommel, M.; Fukuzumi, T.; Bode, J. W. "Cyclic Ketimines as Superior Electrophiles for NHC-Catalyzed Homoenolate Additions with Broad Scope and Low Catalyst Loadings", J. Am. Chem. Soc. 2008, 130, 17266–17267. Link -reviewed in Synfacts 2009, issue 02, 216. Link
(19)	He, M.; Beahm, B. J.; Bode, J. W. "Chiral NHC-Catalyzed Oxodiene Diels−Alder Reactions with alpha-Chloroaldehyde Bisulfite Salts", Org. Lett. 2008, 10, 3817–3820. Link
(18)	Struble, J. R.; Bode, J. W. "A modular synthesis of chiral aminoindanol-derived imidazolium salts", Tetrahedron 2008, 64, 6961–6972. Link
(17)	Ju, L.; Lippert, A. R.; Bode, J. W. "Stereoretentive Synthesis and Chemoselective Amide-Forming Ligations of C-Terminal Peptide alpha-Ketoacids", J. Am. Chem. Soc. 2008, 130, 4253–4255. Link
(16)	Struble, J.R.; Kaeobamrung, J.; Bode, J.W. "Synthesis of an N-Mesityl Substituted Chiral Imidazolium Salt for NHC-Catalyzed Reactions", Org. Lett. 2008, 10, 957–960. Link -reviewed in Synfacts 2008, issue 06, 645. Link
(15)	He, M.; Bode, J. W. "Enantioselective, NHC-Catalyzed Bicyclo-beta-Lactam Formation via Direct Annulations of Enals and Unsaturated N-Sulfonyl Ketimines", J. Am. Chem. Soc. 2008, 130, 418–419. Link -reviewed in Synfacts 2008, issue 03, 307. Link
(14)	Bode, J. W.; Sohn, S. S. "N-Heterocyclic Carbene-Catalyzed Redox Amidations of alpha-Functionalized Aldehydes with Amines", J. Am. Chem. Soc. 2007, 129, 13798–13799. Link
(13)	Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. "Enantioselective, Cyclopentene-Forming Annulations via NHC-Catalyzed Benzoin–Oxy-Cope Reactions", J. Am. Chem. Soc. 2007, 129, 3520–3521. Link -reviewed in Synfacts 2007, issue 05, 545. Link
(12)	He, M.; Uc, G. J.; Bode, J. W. "Chiral, N-Heterocyclic Carbene Catalyzed Oxodiene Diels-Alder Reactions with Low Catalyst Loadings", J. Am. Chem. Soc. 2006, 128, 15088–15089. Link -reviewed in Synfacts 2007, issue 01, 100. Link
(11)	Review article: Bode, J. W. "Emerging Methods for the Synthesis of Amide and Peptide Bonds", Curr. Opin. Drug Discov. Devel. 2006, 9, 765–775. PubMed
(10)	Lippert, A. R.; Kaeobamrung, J.; Bode, J. W. "Synthesis of Oligosubstituted Bullvalones: Shapeshifiting Molecules Under Basic Conditions ", J. Am. Chem. Soc. 2006, 128, 14738–14739. Link
(9)	Sohn, S. S.; Bode, J. W. "N-Heterocyclic Carbene Catalyzed C–C Bond Cleavage in Redox Esterifications of Chiral Formylcyclopropanes", Angew. Chem. Int. Ed. 2006, 6021–6024. Link -reviewed in Synfacts 2006, issue 10, 1060. Link
(8)	He, M.; Struble, J. R.; Bode, J. W. "Highly Enantioselective Azadiene Diels-Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes", J. Am. Chem. Soc. 2006, 128, 8418–8420. Link -reviewed in Synfacts 2006, issue 08, 840. Link
(7)	Carrillo, N.; Davalos, E. A.; Russak, J. A.; Bode, J. W. "Iterative, Aqueous Synthesis of b3-oligopeptides without Coupling Reagents ", J. Am. Chem. Soc. 2006, 128, 1452-1453. Link -Highlight in C&E News. Link
(6)	Bode, J. W.; Fox, R. M.; Baucom, K. D. "Decarboxylative Condensations of alpha-Ketoacids and N-Alkylhydroxylamines: A New Amide Ligation Reaction", Angew. Chem. Int. Ed. 2006, 45, 1248-1252. Link -Highlight in C&E News. Link
(5)	Sohn, S.; Bode, J. W. "Catalytic Generation of Activated Carboxylates from Enals: A Product Determining Role for the Base ", Org. Lett. 2005, 7, 3873-3876. Link -Categorize in Organic Chemistry Portal. Link
(4)	He, M.; Bode, J. W. "Catalytic Synthesis of gamma-Lactams via Direct Annulations of Enals and N-Sulfonylimines", Org. Lett. 2005, 7, 3131–3134. Link -Highlight in Angew. Chem. 2005, 44, 7506. Link
(3)	Bode, J. W. "Reactor, Chem Axon", J. Am. Chem. Soc. 2004, 126, 15317. (Software Review)
(2)	Sohn, S. S.; Rosen, E. L.; Bode, J. W. "N-Heterocyclic Carbene-Catalyzed Generation of Homoenolates: gamma-Butyrolactones by Direct Annulations of Enals and Aldehydes", J. Am. Chem. Soc. 2004, 126, 14370-14371. Link -Highlight in Angew. Chem. 2005, 44, 7506. Link
(1)	Chow, K. Y.-K.; Bode, J. W. "Catalytic Generation of Activated Carboxylates: Direct, Stereoselective Synthesis of beta-Hydroxyesters from Epoxyaldehydes" J. Am. Chem. Soc. 2004, 126, 8126-8127. Link -Highlight in Angew. Chem. 2005, 44, 7506. Link
	Undergraduate, Graduate, and Postdoctoral Publications Suzuki, K.; Takikawa, H.; Hachisu, Y.; Bode, J. W. "Isoxazole-directed pinacol rearrangement: stereocontrolled approach to angular stereogenic centers", Angew. Chem. Int. Ed. 2007, 46, 3252–3254. Link Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. " Catalytic, Enantioselective Crossed Aldehyde–Ketone Benzoin Cyclizations”, Angew. Chem. Int. Ed. 2006, 45, 3492–3494. Link Hachisu, Y.; Bode, J. W.; Suzuki, K. "Thiazolium Ylide Catalyzed Intramolecular Aldehyde--Ketone Benzoin-Forming Reactions: Substrate Scope" Adv. Syn. Cat. 2004, 1097–1100. Link Matsuura, T.; Bode, J. W.; Hachisu, Y.; Suzuki, K. "Molecular Sieve (MS 4A) Promoted Cyclocondensation of Hindered, Aromatic Nitrile Oxides and Cyclic Diketones under Mild Conditions", Synlett 2003, 1746-1748. Link Hachisu, Y.; Bode, J. W.; Suzuki, K. "Catalytic Intramolecular Aldehyde-Ketone Benzoin Reactions: A Novel Synthesis of Functionalized Preanthraquinones", J. Am. Chem. Soc. 2003, 125, 8432-8433. Link Bode, J. W.; Hachisu, Y.; Matsuura, T.; Suzuki, K. Amine-Promoted Cyclocondensation of Highly Substituted Aromatic Nitrile Oxides with Diketones", Tetrahedron Lett. 2003, 44, 3555-3558. Link Bode, J. W.; Suzuki K. "Structural Incongruities of Coleophomone Natural Products: Insights by Total Synthesis of a Semi-Synthetic Derivative" Tetrahedron Lett. 2003, 44, 3559-3563. Link Bode, J. W.; Hachisu, Y.; Matsuura, T.; Suzuki, K. "Facile Construction and Divergent Transformation of Polycyclic Isoxazoles: Direct Access to Polyketide Architectures", Org. Lett. 2003, 5, 391-394. Link Bode, J. W.; Uekusa, H.; Suzuki, K. "Rearrangement Promoted Cascade Reactions for the Stereoselective Synthesis of Highly Functionalized Polycycles", Org. Lett. 2003, 5, 395-398. Link Bode, J. W.; Gauthier, D. R.; Carreira, E. M. "Facile Enantioselective Synthesis of a Key Homoallylic Alcohol Building Block for Polyketide Synthesis: TiF4-BINOL Catalyzed Allylsilylation", J. Chem. Soc. Chem. Comm. 2001, 2560-2561. Link Bode, J. W.; Carreira, E. M. "Stereoselective Syntheses of Epothilones A and B via Nitrile Oxide Cycloadditions and Related Studies", J. Org. Chem. 2001, 66, 6410-6424. Link Bode, J. W.; Carreira, E. M. "A Mild and Chemoselective Method for the Reduction of Conjugated Isoxazolines to Beta-Hydroxy Ketones", Org. Lett. 2001, 3, 1587-1590. Link Bode, J. W.; Fraefel, N.; Muri, D.; Carreira, E. M. "A General Solution to the Modular Synthesis of Polyketide Building Blocks via Kanemasa Hydroxyl-Directed Nitrile Oxide Cycloadditions", Angew. Chem. Int. Ed. 2001, 40, 2082-2085. Link Bode, J. W.; Carreira, E. M. "Stereoselective Syntheses of Epothilones A and B via Hydroxyl Directed Nitrile Oxide Cycloadditions", J. Am. Chem. Soc. 2001, 123, 3611-3612. Link Muri, D.; Bode, J. W.; Carreira, E.M. "A Novel, General Method for the Synthesis of Nitrile Oxides: Dehydration of O-Silylated Hydroxamic Acids", Org. Lett. 2000, 2, 539-541. Link Bode, J. W.; Doyle, M. P.; Protopopova, M. N. Zhou, Q-L. "Intramolecular Regioselective Insertion into Unactivated Carbon-Hydrogen Bonds with Diazoacetates of Primary Alcohols Catalyzed by Chiral Dirhodium(II) Carboxamidates. Highly Enantioselective Total Synthesis of Natural Lignan Lactones." J. Org. Chem. 1996, 61, 9146-9155. Link Doyle, M.P.; Protopopova, M.N. Zhou, Q.-L.; Bode, J. W.; Simonsen, S.H.; Lynch, V. "Optimization of Enantiocontrol for Carbon-Hydrogen Insertion with Chiral Dirhodium(II) Carboxamidates. Synthesis of Natural Dibenzylbutyrolactone Lignans from 3-Aryl-1-Propyl Diazoacetates in High Optical Purity." J. Org. Chem. 1995, 60, 6654-6655. Link Book Chapters Bode, J. W.; Carreira, E. M. "Total Synthesis of Macrolides" in The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; pp 40-63.

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