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Highly Diastereoselective Conjugate Addition to Alkylidene Bis(Sulfoxides): Asymmetric Synthesis of (+)‐ erythro ‐Roccellic Acid
Author(s) -
Brebion Franck,
Delouvrié Bénédicte,
Nájera Francisco,
Fensterbank Louis,
Malacria Max,
Vaissermann Jacqueline
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352356
Subject(s) - diastereomer , conjugate , reactivity (psychology) , chemistry , nucleophile , michael reaction , lewis acids and bases , chelation , addition reaction , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , mathematics , medicine , mathematical analysis , alternative medicine , pathology
Facial stereocontrol is possible in Michael additions of nucleophiles (Nu) to alkylidene bis(sulfoxides), which proceed via nonchelated ( A ) or chelated ( B ) intermediates depending on the addition of an appropriate Lewis acid (LA). This intriguing reactivity could be applied to the first total synthesis of the succinate‐based natural product, (+)‐ erythro ‐roccellic acid.