Acid-induced transannular cyclization of 2-methyl- and 10-methyl-5-cyclodecenone

2-Methyl- and 10-methyl-5-cyclodecenone were made by anionic oxy-Cope rearrangement of the corresponding 1,2-divinylcyclohexanols, and their transannular cyclizations were induced using trifluoroacetic acid. In each case, a single diastereomer of a trans fused bicyclo[4.4.0]decan-1-ol with an equato...

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Bibliographic Details
Published in:Tetrahedron letters 2001-06, Vol.42 (23), p.3815-3817
Main Authors: Chu, Yongliang, White, James B, Duclos, Brian A
Format: Article
Language:English
Subjects:
5-cyclodecenones
oxy-Cope rearrangement
transannular cyclizations
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Summary:2-Methyl- and 10-methyl-5-cyclodecenone were made by anionic oxy-Cope rearrangement of the corresponding 1,2-divinylcyclohexanols, and their transannular cyclizations were induced using trifluoroacetic acid. In each case, a single diastereomer of a trans fused bicyclo[4.4.0]decan-1-ol with an equatorial methyl group was isolated. The methyl substituent at C2 or C10 of the 5-cyclodecenone did not alter the regio- and stereochemistry previously observed for the parent ring system, ( E)-5-cyclodecenone. The relative stereochemistry of the products was determined spectroscopically from J-value analysis and NOE. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)00618-9