A tandem aza-Claisen rearrangement and ring closing metathesis reaction for the synthesis of cyclic allylic trichloroacetamides

Swift, M. D. and Sutherland, A. (2007) A tandem aza-Claisen rearrangement and ring closing metathesis reaction for the synthesis of cyclic allylic trichloroacetamides. Organic Letters, 9(25), pp. 5239-5242. (doi: 10.1021/ol702299c Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland.)

Abstract

A one-pot tandem palladium(II)-catalyzed aza-Claisen rearrangement and ring closing metathesis process has been developed for the efficient synthesis of cyclic allylic trichloroacetamides. The use of chiral Pd(II) catalysts such as (S)-COP-CI during the rearrangement stage results in the preparation of these compounds in excellent yields and in high enantiomeric excess.

• Item Type: Articles
• Keywords: ALCOHOLS AZA-CLAISEN REARRANGEMENT BOND ISOMERIZATION SEQUENCE CATALYST CATALYSTS CATALYTIC ASYMMETRIC REARRANGEMENT Chiral DERIVATIVES DIENES DIRECTED DIHYDROXYLATION DOMINO REACTIONS EFFICIENT LACTAMS METATHESIS OLEFIN METATHESIS ONE-POT ORGANIC-SYNTHESIS rearrangement RING TRICHLOROACETAMIDES
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew
• Authors: Swift, M. D., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• ISSN: 1523-7060