Synthesis 2012; 44(16): 2601-2606
DOI: 10.1055/s-0032-1316577
paper
© Georg Thieme Verlag Stuttgart · New York

Secondary-Amine-Catalyzed Asymmetric Michael Addition of N-tert-Butoxycarbonyl-Protected Oxindoles to Maleimides

Xuena Yang
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127   Email: [email protected]
,
Chuan Wang
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127   Email: [email protected]
,
Qijian Ni
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127   Email: [email protected]
,
Dieter Enders*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127   Email: [email protected]
› Author Affiliations
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

 
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  • 13 For details on the determination of the configuration of the products, see the Supporting Information.