Synthesis 2014; 46(24): 3365-3373
DOI: 10.1055/s-0034-1379044
paper
© Georg Thieme Verlag Stuttgart · New York

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

Ki-Tae Kang
Department of Chemistry, College of Natural Science, Kyonggi University, 154-42 Gwanggyosan-ro, Yeongtong-gu, Suwon, 443-760, Republic of Korea   Fax: +82(31)2531165   eMail: sgkim123@kyonggi.ac.kr
,
Sung-Gon Kim*
Department of Chemistry, College of Natural Science, Kyonggi University, 154-42 Gwanggyosan-ro, Yeongtong-gu, Suwon, 443-760, Republic of Korea   Fax: +82(31)2531165   eMail: sgkim123@kyonggi.ac.kr
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Publikationsverlauf

Received: 08. Juli 2014

Accepted after revision: 06. August 2014

Publikationsdatum:
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).

Supporting Information