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For some recent overviews, see (a) France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis. Chem. Rev. 2003, 103, 2985-3012.
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France, S.1
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0037251137
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Catalytic enantioselective allylation with chiral lewis bases
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(b) Denmark, S. E.; Fu, J. Catalytic Enantioselective Allylation with Chiral Lewis Bases. Chem. Commun. 2003, 167-170.
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Enantioselective acyl transfer using chiral phosphine catalysts
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(c) Vedejs, E.; Daugulis, O.; MacKay, J. A.; Rozners, E. Enantioselective Acyl Transfer Using Chiral Phosphine Catalysts. Synlett 2001, 1499-1505.
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4
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Applications of dialkylaminopyridine (DMAP) catalysts in organic synthesis
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For a recent review, see Murugan, R.; Scriven, E. F. V. Applications of Dialkylaminopyridine (DMAP) Catalysts in Organic Synthesis. Aldrichim. Acta 2003, 36, 21-27.
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Enantioselective staudinger synthesis of β-lactams catalyzed by a planar-chiral nucleophile
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Hodous, B. L.; Fu, G. C. Enantioselective Staudinger Synthesis of β-Lactams Catalyzed by a Planar-Chiral Nucleophile. J. Am. Chem. Soc. 2002, 124, 1578-1579.
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Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids
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Hodous, B. L.; Ruble, J. C.; Fu, G. C. Enantioselective Addition of Alcohols to Ketenes Catalyzed by a Planar-Chiral Azaferrocene: Catalytic Asymmetric Synthesis of Arylpropionic Acids. J. Am. Chem. Soc. 1999, 121, 2637-2638.
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Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. Catalytic, Asymmetric Synthesis of β-Lactams. J. Am. Chem. Soc. 2000, 122, 7831-7832.
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Enantioselective addition of amines to ketenes catalyzed by a planar-chiral derivative of PPY: Possible intervention of chiral bronsted-acid catalysis
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Hodous, B. L.; Fu, G. C. Enantioselective Addition of Amines to Ketenes Catalyzed by a Planar-Chiral Derivative of PPY: Possible Intervention of Chiral Bronsted-Acid Catalysis. J. Am. Chem. Soc. 2002, 124, 10006-10007.
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Non-linear effects and autocatalysis
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Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; Chapt. 4.1
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For a review of nonlinear effects in asymmetric catalysis, see Kagan, H. B.; Luukas, T. O. Non-Linear Effects and Autocatalysis. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Chapt. 4.1.
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Kagan, H.B.1
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Protonation of enolates
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Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; Chapt. 34.2
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For example, see: Yanagisawa, A.; Yamamoto, H. Protonation of Enolates. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Chapt. 34.2.
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Yanagisawa, A.1
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Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter
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Hills, I. D.; Fu, G. C. Catalytic Enantioselective Synthesis of Oxindoles and Benzofuranones that Bear a Quaternary Stereocenter. Angew. Chem., Int. Ed. 2003, 42, 3921-3924,
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Enantioselective construction of quaternary stereocenters: Rearrangements of O-acylated azlactones catalyzed by a planar-chiral derivative of 4-(pyrrolidino)pyridine
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Ruble, J. C.; Fu, G. C. Enantioselective Construction of Quaternary Stereocenters: Rearrangements of O-Acylated Azlactones Catalyzed by a Planar-Chiral Derivative of 4-(Pyrrolidino)pyridine. J. Am. Chem. Soc. 1998, 120, 11532-11533.
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(a) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. A Novel Oxygen-to-Carbon Ester Migration Catalyzed by 4-(Dimethylamino)pyridine in the Benzofuranone Ring System. J. Chem. Soc., Chem. Commun. 1986,1524-1525.
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(b) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. 4-(Dimethylamino)-pyridine as a Catalyst for Carbon Acylation. 2. Control of Carbon vs Oxygen Acylation in Benzofuranones. J. Org. Chem. 1987, 52, 5425-5430.
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Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: Dual activation of the electrophile and the nucleophile
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Mermerian, A. H.; Fu, G. C. Catalytic Enantioselective Synthesis of Quaternary Stereocenters via Intermolecular C-Acylation of Silyl Ketene Acetals: Dual Activation of the Electrophile and the Nucleophile. J. Am. Chem. Soc. 2003, 125, 4050-4051.
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note
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The silyl ketene acetal does not react with the acylpyridinium ion at room temperature.
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18
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The kinetic resolution of allylic alcohols by a non-enzymatic acylation catalyst; application to natural product synthesis
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Bellemin-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. The Kinetic Resolution of Allylic Alcohols by a Non-Enzymatic Acylation Catalyst; Application to Natural Product Synthesis. Chem. Commun. 2000, 1009-1010.
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Kinetic resolution of aryl alkyl carbinols catalyzed by a planar-chiral derivative of DMAP: A new benchmark for non-enzymatic acylation
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(b) Ruble, J. C.; Tweddell, J.; Fu, G. C. Kinetic Resolution of Aryl Alkyl Carbinols Catalyzed by a Planar-Chiral Derivative of DMAP: A New Benchmark for Non-Enzymatic Acylation. J. Org. Chem. 1998, 63, 2794-2795.
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Non-enzymatic kinetic resolution of propargylic alcohols by a planar-chiral DMAP derivative; crystallographic characterization of the acylated catalyst
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Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. Non-Enzymatic Kinetic Resolution of Propargylic Alcohols by a Planar-Chiral DMAP Derivative; Crystallographic Characterization of the Acylated Catalyst. J. Am. Chem. Soc. 1999, 121, 5091-5092.
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The antibody catalysis route to the total synthesis of epothilones
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Sinha, S. C.; Barbas, C. F., III; Lerner, R. A. The Antibody Catalysis Route to the Total Synthesis of Epothilones. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 14603-14608.
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Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Kinetic Resolution of Amines by a Non-Enzymatic Acylation Catalyst. Angew. Chem., Int. Ed. 2001, 40, 234-236.
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Schmalz, H.-G., Ed.; Wiley-VCH: New York
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For an overview of the early breakthroughs, see Somfai, P. Non-Enzymatic Kinetic Resolution of Secondary Alcohols. In Organic Synthesis Highlights IV; Schmalz, H.-G., Ed.; Wiley-VCH: New York, 2000; pp 175-181.
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