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Synthesis 2001(5): 0708-0712
DOI: 10.1055/s-2001-12761
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
Weitere Informationen
Received
25 September 2000
Publikationsdatum:
15. Oktober 2004 (online)
Publikationsverlauf
Publikationsdatum:
15. Oktober 2004 (online)
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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
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References
Unpublished results
13Structures 2aα and 2aβ were optimized with AM1 as implemented in HyperChem® 5.1, using an algorithm of conjugate gradient (Polak-Riviere)