Highly Diastereoselective Conjugate Addition to Alkylidene Bis(Sulfoxides): Asymmetric Synthesis of (+)‐ erythro ‐Roccellic Acid | Zendy

Brebion Franck | Zendy; Delouvrié Bénédicte | Zendy; Nájera Francisco | Zendy; Fensterbank Louis | Zendy; Malacria Max | Zendy; Vaissermann Jacqueline | Zendy

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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.

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