✦ LIBER ✦
A Flexible Common Approach to α-Substituted Serines and Alanines: Diastereoconvergent Syntheses of Sphingofungins E and F
✍ Scribed by Bing Wang; Guo-Qiang Lin
- Book ID
- 102173320
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 252 KB
- Volume
- 2009
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
A flexible common approach for the asymmetric syntheses of sphingofungins E and F is reported, with efficient use of both diastereomers of the Baylis–Hillman adduct in a stereoconvergent manner. Pronounced steric effects of the 2‐substituents in diastereoselective dihydroxylations of (E)‐2‐hydroxymethyl‐2,3‐alkenoates were observed. This strategy also allowed full control over the absolute configurations of the quaternary stereocenters in α‐substituted amino acids through tunable site‐specific adjustment of oxidation states.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)