A Flexible Common Approach to α‐Substituted Serines and Alanines: Diastereoconvergent Syntheses of Sphingofungins E and F | Zendy

Wang Bing | Zendy; Lin GuoQiang | Zendy

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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)

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