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Conjugate Additions to Alkylidene Bis(Sulfoxides)
Author(s) -
Brebion Franck,
Vincent Guillaume,
Chelli Saloua,
Kwasnieski Ophélie,
Najera Francisco,
Delouvrié Bénédicte,
Marek Ilan,
Derat Etienne,
Goddard JeanPhilippe,
Malacria Max,
Fensterbank Louis
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000904
Subject(s) - conjugate , chemistry , mathematics , mathematical analysis
A general study on the conjugate addition of anionic nucleophiles to alkylidene bis(sulfoxides) is presented. Alkoxides gave high yielding and diastereoselective addition reactions , which could be influenced by solvents and the counteranion. Azides provided an interesting entry into sulfinyl‐substituted triazoles. Organometallics, mainly copper reagents, proved also to be valuable nucleophiles, and complete inversion of the stereoselectivity was achieved in the addition reaction with the latter. Modelizations provide a rationale for the observed diastereoselectivity.