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

doi:10.1055/s-2001-12761

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Synthesis 2001(5): 0708-0712
DOI: 10.1055/s-2001-12761

PAPER

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;

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Publication History

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

Abstract
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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.

Key words

Birch alkylation - decalins - 1,4-dienes - epoxidation - directing effect

References

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12

Unpublished results

13

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