'meso-selective' functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation
'meso-selective' functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation
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DOI：
10.1016/s0040-4039(02)00154-5
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发表时间：
2002-03-11
影响因子：
1.8
通讯作者：
Menet, CJ
中科院分区：
文献类型：
--
作者：
Bragg, RA;Clayden, J;Menet, CJ
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.
