Issue 44, 2012

Enantioselective construction of multifunctionalized spirocyclohexaneoxindoles through organocatalytic Michael–Aldol cyclization of isatin derived alkenes with linear dialdehydes

Abstract

Optically active spirocyclohexaneoxindole motifs are very important building blocks for preparations of biologically active complexes, natural products, and pharmaceutical compounds. Herein, we report the syntheses of enantiopure spirocyclohexaneoxindoles through domino Michael–Aldol reactions between isatin derived alkenes and pentane-1,5-dial in the presence of diphenylprolinol silyl ether as an aminocatalyst. As a result, a series of multistereogenic and functionalized spirocyclohexaneoxindoles have been obtained in good yields with moderate diastereoselectivities and excellent enantioselectivities. In addition, electronic circular dichroism (ECD) spectroscopy and time-dependent density functional theory (TD-DFT) were used to investigate the rational structures of spirocyclohexaneoxindoles.

Graphical abstract: Enantioselective construction of multifunctionalized spirocyclohexaneoxindoles through organocatalytic Michael–Aldol cyclization of isatin derived alkenes with linear dialdehydes

Supplementary files

Article information

Article type
Paper
Submitted
25 Jun 2012
Accepted
13 Sep 2012
First published
14 Sep 2012

Org. Biomol. Chem., 2012,10, 8794-8799

Enantioselective construction of multifunctionalized spirocyclohexaneoxindoles through organocatalytic Michael–Aldol cyclization of isatin derived alkenes with linear dialdehydes

X. Huang, Z. Liu, Z. Geng, S. Zhang, Y. Wang and X. Wang, Org. Biomol. Chem., 2012, 10, 8794 DOI: 10.1039/C2OB26205C

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