Synthesis 2001(5): 0708-0712
DOI: 10.1055/s-2001-12761
PAPER
© Georg Thieme Verlag Stuttgart · New York

Epoxidation of 8a-Alkyl-1,2,3,4,6,8a-hexahydronaphthalen-1-ones and -1-ols

Guillermo R. Labadie, Raquel M. Cravero, Manuel Gonzalez-Sierra*
IQUIOS-(Instituto de Química Orgánica de Síntesis), Departamento de Química Orgánica, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531-S2000LRK-Rosario-Santa Fe, Argentina
Fax: +54(341)4370477; e-Mail: mgsierra@fbioyf.unr.edu.ar;
Further Information

Publication History

Received 25 September 2000
Publication Date:
15 October 2004 (online)

Abstract

The regio- and diastereoselectivities of the epoxidations of decalin-1,4-dienones and dienols obtained from the Birch reductive alkylation of different α-tetralones is described. They appear to depend on the steric approach control of the peroxide and show an important contribution to the directing effect of homoallylic alcohols.

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Unpublished results

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Structures 2aα and 2aβ were optimized with AM1 as implemented in HyperChem® 5.1, using an algorithm of conjugate gradient (Polak-Riviere)