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

Mukund P. Sibi; Miguel A. Guerrero

doi:10.1055/s-2005-865319

PAPER

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;

Abstract

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Abstract

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

Key words

radical reactions - chiral Lewis acid - lactones - conjugate additions - enantioselective reactions

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References

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8 The compound was prepared from optically pure epichlorohydrin

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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.

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