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Olefination of N ‐Sulfinylimines under Mild Conditions
Author(s) -
Dhara Shubhendu,
Diesendruck Charles E.
Publication year - 2017
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.201601577
Subject(s) - chemistry , carbanion , phosphonate , selectivity , yield (engineering) , sodium hydride , aryl , base (topology) , sulfoxide , hydride , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , alkyl , hydrogen , mathematical analysis , materials science , mathematics , metallurgy
A very simple and efficient diastereoselective synthesis of 1,2‐disubstituted alkenes has been achieved under mild conditions. Sulfoxide stabilised N ‐sulfinylimines reacted with in‐situ‐generated phosphonate carbanions to give 1,2‐disubtituted alkenes in good to excellent yields. Different aryl phosphonates reacted with a range of electronically diverse N ‐sulfinylimines to give alkenes with >99:1 E selectivity. The most important feature of this protocol is that the reaction can be carried out at room temperature with inexpensive sodium hydride as the most effective base to generate the reactive phosphonate carbanions, and producing the alkenes with E selectivity in up to 85 % isolated yield.