Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 6, Pages 2289-2300Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3020648
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Funding
- CNRS
- ICSN
- [ANR-11-BS07-006-01]
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The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.
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