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Letter

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

Supporting Info

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.

Org. Lett., 2007, 9 (10), pp 1931–1934

DOI: 10.1021/ol070482k

Publication Date (Web): April 11, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, michael.greaney@ed.ac.uk

Abstract

The intramolecular iodo-aldol cyclization of α-substituted enoate aldehydes and ketones is described. Using prochiral starting materials, the reaction produces hetero- and carbocycles containing quaternary centers adjacent to secondary or tertiary centers. The reactions occur in good yields and are highly selective for the trans-products, having the hydroxyl and iodomethyl groups on opposite faces of the ring system.

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Published In Issue May 10, 2007
Received February 25, 2007

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Letter

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Inspirations, Discoveries, and Future Perspectives in Total Synthesis

Direct Arylation of Oxazoles at C2. A Concise Approach to Consecutively Linked Oxazoles

A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones

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