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A Flexible Common Approach to α‐Substituted Serines and Alanines: Diastereoconvergent Syntheses of Sphingofungins E and F
Author(s) -
Wang Bing,
Lin GuoQiang
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900772
Subject(s) - chemistry , stereocenter , steric effects , hydroxymethyl , diastereomer , adduct , stereochemistry , enantioselective synthesis , organic chemistry , catalysis
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)