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- W2000281008 abstract "We have developed highly diastereoselective silver-catalyzed direct aldol reactions of benzophenone glycine imines with aromatic, heteroaromatic and aliphatic aldehydes. Protection of the secondary alcohol in the aldol product in situ with di-tert-butyl dicarbonate was applied to effectively circumvent the retro-aldol process resulting in improved yields of the aldol products. Only a catalytic amount of base, lithium tert-butoxide, is required since tert-butoxide is regenerated during the Boc protection. Computational studies support a stereochemical model in which the axially-oriented nitrogen atom of the imino (Z)-enolates coordinates the silver center in a boat conformation. The highly-ordered transition states favor the formation of the syn aldol products due to the destabilizing interaction between the 1,3-pseudoaxial alkoxyl group and the aldehyde substituent in the anti isomer." @default.
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- W2000281008 date "2014-11-20" @default.
- W2000281008 modified "2023-10-16" @default.
- W2000281008 title "Catalytic<i>syn</i>-Selective Direct Aldol Reactions of Benzophenone Glycine Imine with Aromatic, Heteroaromatic and Aliphatic Aldehydes" @default.
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- W2000281008 doi "https://doi.org/10.1002/adsc.201400639" @default.
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