Synthesis of Aryl Glycines by the α Arylation of Weinreb Amides | Zendy

Hirner Sebastian | Zendy; Panknin Olaf | Zendy; Edefuhr Magnus | Zendy; Somfai Peter | Zendy

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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.

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