'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

共 45 条

[21] Configurational stability and stereospecificity in the reactions of amide-stabilised organolithiums: A non-stereospecific tin-lithium exchange [J].

Clayden, J ;

Pink, JH .

TETRAHEDRON LETTERS, 1997, 38 (14) :2565-2568

[22] Controlling the regioselectivity of lithiation using kinetic isotope effects: Deuterium as a protecting group for carbon [J].

Clayden, J ;

Pink, JH ;

Westlund, N ;

Wilson, FX .

TETRAHEDRON LETTERS, 1998, 39 (46) :8377-8380

[23]

CLAYDEN J, 2002, IN PRESS CHEM COMMUN, V38

[24]

Derwing C, 1999, EUR J ORG CHEM, V1999, P3519

[25]

Derwing C, 1996, SYNTHESIS-STUTTGART, P149

[26] A mechanistic and structural investigation of the (-)-sparteine mediated asymmetric benzylic lithiation substitution reactions of N-boc-N-(p-methoxyphenyl)benzylamine [J].

Faibish, NC ;

Park, YS ;

Lee, S ;

Beak, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (48) :11561-11570

[27] SUBSTITUTION ALPHA TO NITROGEN IN DIBENZYLAMINE VIA CARBANION INTERMEDIATES [J].

FRASER, RR ;

BOUSSARD, G ;

POSTESCU, ID ;

WHITING, JJ ;

WIGFIELD, YY .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (07) :1109-1115

[28] A proposal for (slight) modification of the Hughes-Ingold mechanistic descriptors for substitution reactions [J].

Gawley, RE .

TETRAHEDRON LETTERS, 1999, 40 (23) :4297-4300

[29] ALKYLATION OF 2-LITHIO-N-METHYLPIPERIDINES AND 2-LITHIO-N-METHYLPYRROLIDINES - SCOPE, LIMITATIONS, AND STEREOCHEMISTRY [J].

GAWLEY, RE ;

ZHANG, QH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5763-5769

[30] The steric course of SE2 reactions of unstabilized α-aminoorganolithiums:: Distinguishing between SET and polar mechanisms [J].

Gawley, RE ;

Low, E ;

Zhang, QH ;

Harris, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3344-3350

← 1 2 3 4 5 →