Synthesis 2005(9): 1528-1532  
DOI: 10.1055/s-2005-865319
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Radical Methods for Lactone Synthesis: Use of Unprotected Haloalcohols as Radical Precursors

Mukund P. Sibi*, Miguel A. Guerrero
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105, USA
Fax: +1(701)2311057; e-Mail: Mukund.Sibi@ndsu.edu;
Further Information

Publication History

Received 14 March 2005
Publication Date:
18 April 2005 (online)

Abstract

We have developed an efficient free radical method for the synthesis of enantioenriched 6- and 7-membered lactones in one synthetic operation.

10

Note the change in priority for compound 5b. The radical reaction occurs from the same face for all compounds.

11

This reaction proceeds with 39% ee when magnesium bromide is used as the Lewis acid. See ref. 5.