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Synthesis 2015; 47(23): 3805-3812
DOI: 10.1055/s-0035-1560347
DOI: 10.1055/s-0035-1560347
paper
Enantioselective Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted (E)-2-oxobut-3-enoates
Further Information
Publication History
Received: 27 June 2015
Accepted after revision: 28 August 2015
Publication Date:
01 October 2015 (online)
Abstract
An organocatalytic cascade Michael addition-cyclization reaction of cyclopentane-1,2-dione with substituted (E)-2-oxobut-3-enoates, creating two stereocenters and giving bicyclic hemiacetals 3 in excellent yield (up to 93%) and enantioselectivity (up to 96% ee) was developed. From 2-chlorophenyl-substituted (E)-2-oxobut-3-enoate, the adduct revealed pseudo-atropisomerism from the hindered rotation of the phenyl ring. The hemiacetal 3 was reduced with Et3SiH and Lewis acid affording substituted 1,2-cyclopentanedione 8, and disilylated with an excess of TMSOTf and Et3N to the dienol disilyl ether 9.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560347.
- Supporting Information
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