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There are numerous examples of direct aldol reactions using aldol donors bearing electron-withdrawing α-substituents that are readily enolized under mild basic conditions
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There are numerous examples of direct aldol reactions using aldol donors bearing electron-withdrawing α-substituents that are readily enolized under mild basic conditions.
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Direct catalytic asymmetric aldol(-type) reactions using aldol donors in the carboxylic acid oxidation state without electron-withdrawing α-substituents: Alkylnitriles: (a) Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757. Activated amides:
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Direct catalytic asymmetric aldol(-type) reactions using aldol donors in the carboxylic acid oxidation state without electron-withdrawing α-substituents: Alkylnitriles: (a) Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757. Activated amides:
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Direct catalytic asymmetric aldol reaction of thiazolidinethiones in which the use of a stoichiometric amount of silylating reagent was essential: Evans, D. A, Downey, C. W, Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706
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Direct catalytic asymmetric aldol reaction of thiazolidinethiones in which the use of a stoichiometric amount of silylating reagent was essential: Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706.
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The cross-aldol reaction of aldehydes via asymmetric organocatalysis provides a useful methodology for the synthesis of polyols and sugars. Selected examples: (a) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752.
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Asymmetric aldol reaction of thioamides with a stoichiometric chiral source: (a) Cinquini, M.; Manfredi, A.; Molinari, H.; Restelli, A. Tetrahedron 1985, 41, 4929.
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See the Supporting Information
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See the Supporting Information.
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Aromatic aldehydes were more reactive in this system, leading to retroaldol reaction and dehydration of the aldol product (e.g., benzaldehyde: 66% yield, 72% ee). Further investigations are currently underway.
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Aromatic aldehydes were more reactive in this system, leading to retroaldol reaction and dehydration of the aldol product (e.g., benzaldehyde: 66% yield, 72% ee). Further investigations are currently underway.
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