Neighboring ortho-hydroxy group directed catalytic asymmetric triple domino reactions of acetaldehyde with (E)-2-(2-nitrovinyl)phenols
Neighboring ortho-hydroxy group directed catalytic asymmetric triple domino reactions of acetaldehyde with (E)-2-(2-nitrovinyl)phenols
No Thumbnail Available
Date
2014-01-01
Authors
Ramachary, Dhevalapally B.
Reddy, P. Srinivasa
Prasad, M. Shiva
Journal Title
Journal ISSN
Volume Title
Publisher
Abstract
Herein we demonstrate the utilization of neighboring ortho-hydroxy group participation in the pretransition state of enamine- and iminium-based triple domino reactions for high reactions rates and asymmetric induction. Enantiomerically pure, drug-like chromanes and tetrahydro-6H-benzo[c]chromenes having three to four contiguous stereocenters are synthesized through triple domino Michael/aldol/oxa-Michael reactions catalyzed by (R)-2- {diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine followed by Wittig and Michael/Wittig-Horner reactions from simple precursors under mild conditions. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Description
Keywords
Asymmetric catalysis,
Michael addition,
Neighboring-group effects,
Organocatalysis,
Phenols
Citation
European Journal of Organic Chemistry. v.2014(15)