Issue 2, 2011

Enantioselective organocatalytic domino Michael–acetalization–Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones

Abstract

Asymmetric domino Michael–acetalization reactions of 2-hydroxynitrostyrene and aldehydes “on water” followed by oxidation providing the cis-3,4-disubstituted dihydrocoumarins with excellent enantioselectivities (up to >99% ee). The variant with glutaraldehyde underwent a highly stereoselective domino Michael–acetalization–Henry reaction to afford the tetrahydro-6H-benzo[c]chromen-6-ones after the subsequent oxidation.

Graphical abstract: Enantioselective organocatalytic domino Michael–acetalization–Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones

Supplementary files

Article information

Article type
Communication
Submitted
06 Oct 2010
Accepted
02 Nov 2010
First published
03 Nov 2010

Org. Biomol. Chem., 2011,9, 382-386

Enantioselective organocatalytic domino Michael–acetalization–Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones

B. Hong, P. Kotame and J. Liao, Org. Biomol. Chem., 2011, 9, 382 DOI: 10.1039/C0OB00834F

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