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Synthesis 2013; 45(20): 2832-2842
DOI: 10.1055/s-0033-1338517
DOI: 10.1055/s-0033-1338517
paper
Enantioselective Michael Addition of 1,3-Diketones to Arenesulfonylalkylindoles: A Flexible Gateway to Optically Active 3-sec-Alkyl-Substituted Indoles Containing a Pyrazole Skeleton
Further Information
Publication History
Received: 04 July 2013
Accepted: 17 July 2013
Publication Date:
07 August 2013 (online)
Abstract
Enantioselective Michael addition of 1,3-diketones to alkylideneindolenines generated in situ from arenesulfonylalkylindoles is described, and a series of optically active C3-alkyl-substituted indole derivatives has been obtained. The resulting adducts can be readily converted into 3-sec-alkyl-substituted indoles containing a pyrazole skeleton, with direct connection between the α- and 4-positions, without decrease of the enantioselectivity.
Key words
asymmetric catalysis - Michael addition - arenesulfonylalkylindoles - 1,3-diketones - pyrazolesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For reviews, see:
For non-asymmetric examples, see:
For asymmetric examples, see:
For selected recent reviews of (thio)urea-based organocatalysis, see:
For seminal examples using the Takemoto catalyst 1e, see:
For the preparation of catalysts 1a–d, see: