Synthesis 2015; 47(07): 1024-1031
DOI: 10.1055/s-0034-1379943
paper
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Domino Michael/Henry Reaction of Indolin-3-ones with o-Formyl-β-nitrostyrenes

Suruchi Mahajan
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
,
Pankaj Chauhan
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
,
Charles C. J. Loh
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
,
Server Uzungelis
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
,
Gerhard Raabe
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
,
Dieter Enders*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: enders@rwth-aachen.de
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Publikationsverlauf

Received: 01. Dezember 2014

Accepted: 02. Dezember 2014

Publikationsdatum:
05. Januar 2015 (online)


Abstract

A highly diastereo- and enantioselective domino Michael/ Henry reaction of 1-acetylindolin-3-ones with o-formyl-(E)-β-nitrostyrenes catalyzed by low loading of a quinine-derived amine-squaramide provides the corresponding indolin-3-one derivatives bearing four adjacent stereogenic centers in good to high yields and with excellent stereo­selectivities.

Supporting Information