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Three‐Component Coupling Reactions of Silyl Glyoxylates, Vinyl Grignard Reagent, and Nitroalkenes: An Efficient, Highly Diastereoselective Approach to Nitrocyclopentanols
Author(s) -
Boyce Gregory R.,
Johnson Jeffrey S.
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003470
Subject(s) - chapel , chemistry , art , library science , art history , computer science
Quick and easy : A regio‐ and stereoselective three‐component coupling reaction generates functionalized ( Z )‐silyl enol ethers through a vinylation/[1,2]‐Brook rearrangement/vinylogous Michael reaction cascade. These adducts can then undergo a diastereoselective deprotection/intramolecular Henry sequence to rapidly assemble densely functionalized nitrocyclopentanols with three contiguous stereocenters (see scheme; TES=triethylsilyl).