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

Ryan A. Bragg, Jonathan Clayden*, Christel J. Menet

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

14 Citations (Scopus)

Abstract

Lithiation and methylation of amide and carbamate derivatives of α-methylbenzylamine proceeds with high diastereoselectivity in favour of meso bis-α-methylbenzylamine derivatives. Carboxylation of the intermediate organolithium is also diastereoselective, and with N-Boc p-methoxy-α-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.

Original languageEnglish
Pages (from-to)1955-1959
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number11
Early online date30 Jan 2002
DOIs
Publication statusPublished - 11 Mar 2002

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