'meso-selective' functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation

被引：12

作者：

Bragg, RA ^{[1
]}

Clayden, J ^{[1
]}

Menet, CJ ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(02)00154-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiation and methylation of amide and carbamate derivatives of alpha-methylbenzylamine proceeds with high diastereoselectivity in favour of meso bis-alpha-methylbenzylamine derivatives, Carboxylation of the intermediate organolithium is also diastereoselective, and with N-Boc p-methoxy-alpha-methylbenzylamine as starting material, oxidative cleavage provides a new asymmetric route to phenylglycine. Other electrophiles give a range of stereochemical outcomes, apparently depending on the stereospecificity of their reactions with a pair of diastereoisomeric organolithiums of low to moderate configurational stability. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1955 / 1959

页数：5

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