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A New Route to Highly Enantiomerically Enriched ( Z )‐(1‐Methyl‐2‐butenyl)boronic Esters
Author(s) -
Stürmer Rainer
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199000591
Subject(s) - racemization , kinetic resolution , chemistry , boron , resolution (logic) , stereochemistry , organic chemistry , medicinal chemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science
It's certainly a stroke of luck that the chiral borate 2 differentiates just one isomer with high kinetic diastereoselectivity from a racemic mixture of the Grignard compound 1 , which has a fluxional structure. The reaction leading to the boronic ester 3 is a combination of a racemization due to a 1,3‐metallotropic shift with the kinetic resolution of a racemate.