A three-step tandem process for the synthesis of bicyclic gamma-lactams

McGonagle, F. I., Brown, L., Cooke, A. and Sutherland, A. (2010) A three-step tandem process for the synthesis of bicyclic gamma-lactams. Organic and Biomolecular Chemistry, 8(15), pp. 3418-3425. (doi: 10.1039/c004695g)

Abstract

A one-pot, three-step tandem process has been developed for the direct synthesis of functionalised bicyclic [3.3.0], [4.3.0] and [5.3.0] gamma-lactams from simple allylic trichloroacetimidates. The process involves a palladium(II) mediated Overman rearrangement followed by the use of Grubbs first generation complex which catalyzes both a ring closing metathesis reaction and a Kharasch cyclization. As well as exploring the scope of this process for the synthesis of a range of functionalised bicyclic g-lactams, the use of chiral palladium(II) catalysts during the Overman rearrangement for the enantioselective synthesis of the bicyclic g-lactams is also demonstrated.

• Item Type: Articles
• Keywords: ALLYLIC ALCOHOLS CATALYTIC ASYMMETRIC REARRANGEMENT CLAISEN REARRANGEMENT COMPLEXES DOMINO REACTIONS ECONOMY IN-SITU METATHESIS-OLEFIN ISOMERIZATION ORGANIC-SYNTHESIS RADICAL CYCLIZATION SEQUENCE
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew
• Authors: McGonagle, F. I., Brown, L., Cooke, A., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic and Biomolecular Chemistry
• ISSN: 1477-0520