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

Ryan A. Bragg; Jonathan Clayden; Christel J. Menet

doi:10.1016/S0040-4039(02)00154-5

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

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

Research output: Contribution to journal › Article › peer-review

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. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	1955-1959
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(02)00154-5
Publication status	Published - 11 Mar 2002

Keywords

Bond cleavage (oxidative; prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.); Asymmetric synthesis and induction; Carboxylation; Lithiation; Methylation; Stereochemistry; Transmetalation (prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.); Amides; Amino acids Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.); Metalation (stannylation; prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.)

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@article{8f195c704cb74c10bb7e5f55cb36972f,

title = "'meso-Selective' functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation",

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. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

keywords = "Bond cleavage (oxidative; prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.); Asymmetric synthesis and induction; Carboxylation; Lithiation; Methylation; Stereochemistry; Transmetalation (prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.); Amides; Amino acids Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.); Metalation (stannylation; prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.)",

author = "Bragg, {Ryan A.} and Jonathan Clayden and Menet, {Christel J.}",

year = "2002",

month = mar,

day = "11",

doi = "10.1016/S0040-4039(02)00154-5",

language = "English",

volume = "43",

pages = "1955--1959",

journal = "Tetrahedron Letters",

issn = "1873-3581",

publisher = "Elsevier BV",

number = "11",

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TY - JOUR

T1 - 'meso-Selective' functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation

AU - Bragg, Ryan A.

AU - Clayden, Jonathan

AU - Menet, Christel J.

PY - 2002/3/11

Y1 - 2002/3/11

N2 - 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. © 2002 Elsevier Science Ltd. All rights reserved.

AB - 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. © 2002 Elsevier Science Ltd. All rights reserved.

KW - Bond cleavage (oxidative; prepn. of phenylglycines via diastereoselective reactions of organolithium methylbenzylamine derivs.); Asymmetric synthesis and induction; Carboxylation; Lithiation; Methylation; Stereochemistry; Transmetalation (prepn. of phenyl

U2 - 10.1016/S0040-4039(02)00154-5

DO - 10.1016/S0040-4039(02)00154-5

M3 - Article

SN - 1873-3581

VL - 43

SP - 1955

EP - 1959

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

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

Abstract

Keywords

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