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Review | Special issue | Vol 76, No. 2, 2008, pp.949-979
Published online, 4th August, 2008
DOI: 10.3987/REV-08-SR(N)7
■ Recent Advances in Lewis Base-Catalyzed, Stereoselective Tandem Aldol β- and γ-Lactonizations

Vikram C. Purohit, Andrea S. Matla, and Daniel Romo*

*Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX, 77842-3012, USA

Abstract

Stereoselective methods for the synthesis of β-lactones involving a Lewis base-promoted (nucleophile-promoted) aldol-lactonization manifold have continued to expand since the initial reports of Bormann and Wegler in the late 1960’s and later by Wynberg and Staring in the early 1980’s. This review will cover these developments including enantioselective versions of these processes. Cinchona alkaloids and various pyridine derivatives have been used most extensively to expand the repertoire of β-lactones accessible by this process. Furthermore, recent advances in the development of a3-d3-ümpolung pathways using N-heterocyclic carbenes have also enabled access to previously unattainable manifolds for the stereoselective synthesis of both β- and γ-lactones via aldol-lactonization pathways. This review covers literature in this area in the period from 1967- June 2008.