Sequential Double α-Arylation of N-Allylureas by Asymmetric Deprotonation and N→C Aryl Migration

被引：43

作者：

Tetlow, Daniel J.

Hennecke, Ulrich

Raftery, James

Waring, Michael J.

Clarke, David S.

Clayden, Jonathan ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

LITHIATION-SUBSTITUTION SEQUENCES; DEAROMATISING CYCLIZATION; ORGANOMETALLIC REAGENTS; CHIRAL AMINES; ORGANOLITHIUMS; ISOMERIZATION; RUTHENIUM; KETONES;

D O I：

10.1021/ol102155h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic alpha carbon. From the alpha-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control.

引用

收藏

页码：5442 / 5445

页数：4

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