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Neighboring ortho ‐Hydroxy Group Directed Catalytic Asymmetric Triple Domino Reactions of Acetaldehyde with ( E )‐2‐(2‐Nitrovinyl)phenols
Author(s) -
Ramachary Dhevalapally B.,
Reddy P. Srinivasa,
Prasad M. Shiva
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402182
Subject(s) - chemistry , aldol reaction , iminium , domino , trimethylsilyl , michael reaction , stereocenter , organocatalysis , wittig reaction , enamine , pyrrolidine , stereochemistry , asymmetric induction , medicinal chemistry , catalysis , enantioselective synthesis , organic chemistry
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‐6 H ‐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.