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Synthesis 2014; 46(24): 3365-3373
DOI: 10.1055/s-0034-1379044
DOI: 10.1055/s-0034-1379044
paper
One-Pot Catalytic Enantioselective Synthesis of Functionalized Tetrahydroquinolines by Aza-Michael/Michael Cascade Reactions of N-Protected 2-Aminophenyl α,β-Unsaturated Esters with Nitroolefins
Further Information
Publication History
Received: 08 July 2014
Accepted after revision: 06 August 2014
Publication Date:
10 September 2014 (online)
Abstract
A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biological properties has been developed by means of asymmetric organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl α,β-unsaturated esters in the presence of a chiral thiourea catalyst. The reaction gave the corresponding highly functionalized tetrahydroquinolines in good yields, excellent diastereoselectivities (>30:1 dr), and high enantioselectivities (≤99% ee).
Key words
organocatalysis - Michael additions - cascade reactions - asymmetric synthesis - tetrahydroquinolinesSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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Du and co-workers used a bifunctional cinchona squaramide derivative as the catalyst:
We used a bifunctional cinchona thiourea derivative as the catalyst: