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Synthesis of Aryl Glycines by the α Arylation of Weinreb Amides
Author(s) -
Hirner Sebastian,
Panknin Olaf,
Edefuhr Magnus,
Somfai Peter
Publication year - 2008
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.200704689
Subject(s) - lithium diisopropylamide , umpolung , amide , chemistry , reagent , iminium , lithium (medication) , aryl , nucleophile , lithium amide , base (topology) , transmetalation , nucleophilic addition , organic chemistry , combinatorial chemistry , medicinal chemistry , ion , enantioselective synthesis , catalysis , mathematics , mathematical analysis , deprotonation , endocrinology , medicine , alkyl
A rare example of the umpolung of an enolate forms the basis of the title reaction. In this procedure, a Grignard reagent is added to the iminium ion formed from the Weinreb amide upon treatment with a base (see scheme). When a chiral amide was used as the starting material, the nucleophilic addition proceeded with high diastereoselectivity. LDA = lithium diisopropylamide.