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Diastereoselective Pinacol Coupling Reactions of α ‐Ketoamides Mediated by SmI 2 : Synthesis of Enantiomerically Pure R and S Quaternary Tartaric Acids
Author(s) -
Kim Sam Min,
Byun Il Suk,
Kim Yong Hae
Publication year - 2000
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/(sici)1521-3773(20000218)39:4<728::aid-anie728>3.0.co;2-6
Subject(s) - pinacol , enantiopure drug , tartaric acid , coupling (piping) , chemistry , hydrolysis , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , metallurgy , citric acid
Chiral auxiliaries of the type Xc influence the pinacol coupling reaction of α ‐ketoamides in the presence of SmI 2 , hexamethyl phosphoramide, and t BuOH to give the pinacol products with high diastereoselectivity (up to >99%, see scheme). These products can then be hydrolyzed to give the enantiopure ( S , S )‐ or ( R , R )‐2,3‐dialkyltartaric acids. TBPS= tert ‐butyldiphenylsilyl.