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Highly Diastereoselective Synthesis of vicinal Quaternary and Tertiary Stereocenters Using the Iodo-aldol Cyclization

Frederic Douelle, Amy S. Capes and Michael F. Greaney*

*University of Edinburgh, School of Chemistry, Joseph Black Building, King's Buildings, West Mains Rd., Edinburgh EH9 3JJ, U.K., Email: michael.greaneyed.ac.uk

F. Douelle, A. S. Capes, M. F. Greaney, Org. Lett., 2007, 9, 1931-1934.

DOI: 10.1021/ol070482k (free Supporting Information)


Abstract

An intramolecular iodo-aldol cyclization of prochiral α-substituted enoate aldehydes and ketones produces hetero- and carbocycles containing quaternary centers adjacent to secondary or tertiary centers. The reactions occur in good yields and are highly trans-selective with hydroxyl and iodomethyl groups on opposite faces of the ring system.

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Key Words

Cyclopentanes, Cyclohexanes, Pyrrolidines, Piperidines, Tetrahydrofurans, Tetrahydropyrans


ID: J54-Y2007-1420