Desymmetrization of metallated cyclohexadienes with chiral N-tert-butanesulfinyl imines

Maji MS, Frohlich R, Studer A

Research article (journal)

Abstract

This communication describes the desymmetrization of various achiral metallated cyclohexadienes with a series of chiral N-tert-butanesulfinyl imines. Depending on the metal used, either the symmetrical diene (dicyclohexadienyl-zinc) or the desymmetrized diene (cyclohexadienyl-MgCl) is obtained in a good regioselectivity with excellent diastereoselectivity. The products formed should be useful building blocks for natural product synthesis. The symmetrical 1,4-dienes are readily oxidized to the corresponding diarylmethylamine derivatives.

Details zur Publikation

Pages: 4
Release year: 2008
Language in which the publication is written: English