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. 2010 Mar 3;51(9):1322.
doi: 10.1016/j.tetlet.2009.12.139.

Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles

Derong Ding  1 , Cong-Gui Zhao
Affiliations

Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles

Derong Ding et al. Tetrahedron Lett. .

Abstract

2-Amino-8-oxo-tetrahydro-4H-chromene-3-carbonitriles were synthesized for the first time from a tandem Michael addition - cyclization reaction between cyclohexane-1,2-dione and benzylidenemalononitriles. An enantioselective synthesis of these compounds was achieved in moderate ee values (up to 63% ee) by using a cinchona alkaloid-derived thiouea catalyst.

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Figures

Figure 1
Figure 1
Chiral catalyst screened for the enantioselective synthesis of 3a
Scheme 1
Scheme 1
Proposed mechanism for the formation of product 3
See this image and copyright information in PMC

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