Conjugate addition of amines to vinyl sulfoximides:: a general method for the synthesis of β-amino sulfoximides

被引：5

作者：

Tye, H ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem Sci, Birmingham B15 2TT, W Midlands, England

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(02)02326-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a range of beta-amino sulfoximide derivatives is described. The conjugate addition of simple amines or amino acids to N-tosyl phenyl vinyl sulfoximide was achieved in moderate to good yield (41-95%). Electron poor nucleophiles such as tosyl amide or benzyl carbarnate were found to be unreactive under analogous conditions. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：9421 / 9423

页数：3

共 7 条

[1] ASYMMETRIC SELECTION VIA ADDITION .2. OPTICALLY-ACTIVE SULFOXIMIDES [J].

ANNUNZIATA, R ;

CINQUINI, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (07) :1684-1686

[2] A study of the functional group compatibility of sulfoximination methods [J].

Cren, S ;

Kinahan, TC ;

Skinner, CL ;

Tye, H .

TETRAHEDRON LETTERS, 2002, 43 (15) :2749-2751

[3] ASYMMETRIC-SYNTHESIS OF CHIRAL ORGANOSULFUR COMPOUNDS USING N-SULFINYLOXAZOLIDINONES [J].

EVANS, DA ;

FAUL, MM ;

COLOMBO, L ;

BISAHA, JJ ;

CLARDY, J ;

CHERRY, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :5977-5985

[4] Cu(I)-catalyzed sulfoximination [J].

Müller, JFK ;

Vogt, P .

TETRAHEDRON LETTERS, 1998, 39 (27) :4805-4806

[5] ASYMMETRIC INTRAMOLECULAR CONJUGATE ADDITION OF AMINES TO CHIRAL VINYL SULFOXIMIDES - TOTAL SYNTHESIS OF (R)-(+)-CARNEGINE AND (S)-(-)-CARNEGINE [J].

PYNE, SG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (23) :1686-1687

[6]

Reggelin M, 1998, ANGEW CHEM INT EDIT, V37, P2883, DOI 10.1002/(SICI)1521-3773(19981102)37:20<2883::AID-ANIE2883>3.0.CO

[7]

2-Y

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