Dihydroxyacetone variants in the organocatalytic construction of carbohydrates: mimicking tagatose and fuculose aldolases

…, S Mitsumori, K Albertshofer, F Tanaka…

Index: Suri, Jeff T.; Mitsumori, Susumu; Albertshofer, Klaus; Tanaka, Fujie; Barbas III, Carlos F. Journal of Organic Chemistry, 2006 , vol. 71, # 10 p. 3822 - 3828

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Citation Number: 128

Abstract

Dihydroxyacetone variants have been explored as donors in organocatalytic aldol reactions with various aldehyde and ketone acceptors. The protected form of dihydroxyacetone that was chosen for in-depth study was 2, 2-dimethyl-1, 3-dioxan-5-one, 1. Among the catalysts surveyed here, proline proved to be superior in terms of yield and stereoselectivities in the construction of various carbohydrate scaffolds. In a fashion analogous to aldolase ...