Three‐Component Coupling Reactions of Silyl Glyoxylates, Vinyl Grignard Reagent, and Nitroalkenes: An Efficient, Highly Diastereoselective Approach to Nitrocyclopentanols | Zendy

Boyce Gregory R. | Zendy; Johnson Jeffrey S. | Zendy

Premium

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).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research