Issue 8, 2015

Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile

Abstract

2-Amino-3-cyano-4H-chromenes show great potential as novel anticancer agents. Here we report a quinine-catalyzed highly enantioselective formal 4 + 2 cycloaddition of ortho-quinone methides and malononitrile, providing a unique approach to 4-arylvinyl, 4-aryl and 4-vinyl 2-amino-3-cyano-4H-chromenes with excellent yields and enantioselectivities. Moreover, this reaction can be performed in up to 6 mmol scale without any noticeable loss of yield and stereoselectivity.

Graphical abstract: Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile

Supplementary files

Article information

Article type
Communication
Submitted
14 Dec 2014
Accepted
06 Jan 2015
First published
06 Jan 2015

Org. Biomol. Chem., 2015,13, 2247-2250

Author version available

Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile

A. Adili, Z. Tao, D. Chen and Z. Han, Org. Biomol. Chem., 2015, 13, 2247 DOI: 10.1039/C4OB02602K

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