Download PDF
Synfacts 2011(9): 0980-0980  
DOI: 10.1055/s-0030-1261013
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of δ-Lactones via Aldol, Cyclo-propanation, and Ring-Opening Cascade

Contributor(s): Mark Lautens, Jane Panteleev
J. Peed, I. Periñán Domínguez, I. R. Davies, M. Cheeseman, J. E. Taylor, G. Kociok-Köhn, S. D. Bull*
University of Bath, UK
Further Information

Publication History

Publication Date:
19 August 2011 (online)

   Permissions and Reprints
Preview

Significance

The authors describe a reaction sequence to access highly enantiomerically enriched δ-lactones. Using this reaction sequence, products containing up to four contiguous stereocenters could be formed. The reported sequence utilized the Evans auxiliary as a source of chirality in an aldol reaction. Subsequent stereocenters are generated through diastereoselective cyclopropanation and mercury-promoted cyclopropane ring opening.