Asymmetric Synthesis of Polysubstituted 4-Amino- and 3,4-Diaminochromanes with a Chiral Multifunctional Organocatalyst

A series of multifunctional catalysts with two chiral diaminocyclohexane units were developed and successfully applied in the asymmetric oxa-Michael–aza-Henry cascade reaction of salicylaldimines with nitroolefins. This approach provides a simple and efficient entry to polysubstituted chiral 4-amino...

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Bibliographic Details
Published in:Organic letters 2012-05, Vol.14 (9), p.2378-2381
Main Authors: Hou, Wenduan, Zheng, Bo, Chen, Jun, Peng, Yungui
Format: Article
Language:English
Subjects:
Catalysis
Chromans - chemical synthesis
Chromans - chemistry
Molecular Structure
Stereoisomerism
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Summary:A series of multifunctional catalysts with two chiral diaminocyclohexane units were developed and successfully applied in the asymmetric oxa-Michael–aza-Henry cascade reaction of salicylaldimines with nitroolefins. This approach provides a simple and efficient entry to polysubstituted chiral 4-aminobenzopyrans with three consecutive stereocenters and in high yield (up to 97%) with excellent stereoselectivity (up to 98% ee and >99:1 dr). Facile access to the nonsymmetric optically pure 3,4-diaminochromanes was also obtained.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300798t