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Synthesis 2012; 44(16): 2601-2606
DOI: 10.1055/s-0032-1316577
DOI: 10.1055/s-0032-1316577
paper
Secondary-Amine-Catalyzed Asymmetric Michael Addition of N-tert-Butoxycarbonyl-Protected Oxindoles to Maleimides
Further Information
Publication History
Received: 24 May 2012
Accepted: 31 May 2012
Publication Date:
06 July 2012 (online)
Abstract
A secondary-amine-catalyzed asymmetric Michael addition of 3-substituted N-(tert-butoxycarbonyl)oxindoles to maleimides with activation by a Brønsted base gives the corresponding products in high yields (86–98%), excellent diastereomeric ratios (dr > 99:1), and high enantiomeric excesses (86–91% ee).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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For reviews on the asymmetric synthesis of 3-substituted oxindoles, see:
For selected examples of asymmetric Michael additions using oxindoles as nucleophiles, see ref. 2e and:
For selected examples of applications of maleimides in organocatalysis, see refs. 4g, 4s, and:
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For selected examples on SOMO activation, see: