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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