Volume 2017, Issue 8 p. 1184-1190
Full Paper

Olefination of N-Sulfinylimines under Mild Conditions

Shubhendu Dhara

Shubhendu Dhara

Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, 3200003 Haifa, Israel

Search for more papers by this author
Charles E. Diesendruck

Corresponding Author

Charles E. Diesendruck

Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, 3200003 Haifa, Israel

Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, Haifa 3200003, Israel

E-mail: [email protected]

E-mail: [email protected]

http://chemistry.web3.technion.ac.il/members/charles-e-diesendruck/

Search for more papers by this author
First published: 05 January 2017
Citations: 6

Graphical Abstract

Imines are very useful directing groups, and, when coupled with a chiral auxiliary such as a sulfoxide group, powerful tools in total synthesis. In this paper, we show that these groups can be converted very efficiently and diastereoselectively into 1,2-disubstituted alkenes (>99:1 E isomer) under very mild conditions.

Abstract

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.