New syntheses of enantiopure 2-methyl isoserines

被引：13

作者：

Avenoza, A ^{[1
]}

Busto, JH ^{[1
]}

Corzana, F ^{[1
]}

Jiménez-Osés, G ^{[1
]}

París, M ^{[1
]}

Peregrina, JM ^{[1
]}

Sucunza, D ^{[1
]}

Zurbano, MM ^{[1
]}

机构：

[1] Univ La Rioja, UA, Grp Sintesis Quim La Rioja, CSIC,Dept Quim, Logrono 26006, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 01期

关键词：

D O I：

10.1016/j.tetasy.2003.09.051

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Herein we describe the synthesis of the two enantiomerically pure 3-amino-2-hydroxy-2-methylpropionic acids-(S)- and (R)-alpha-methyl isoserines-starting from the chiral diols (S)- and (R)-2,3-dihydroxy-N-methoxy-2,N-dimethylpropionamides, respectively, which were obtained by Sharpless asymmetric dihydroxylation (AD) of the olefin N-methoxy-2,N-dimethylacrylamide with AD-mix alpha or beta as chiral catalytic ligands. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：131 / 137

页数：7

共 24 条

[1] Understanding the unusual regioselectivity in the nucleophilic ring-opening reactions of gem-disubstituted cyclic sulfates.: Experimental and theoretical studies [J].

Avenoza, A ;

Busto, JH ;

Corzana, F ;

García, JI ;

Peregrina, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4506-4513

[2] Enantioselective synthesis of (S)- and (R)-α-methylserines:: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals [J].

Avenoza, A ;

Cativiela, C ;

Corzana, F ;

Peregrina, JM ;

Sucunza, D ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :949-957

[3]

Banerjee A, 1997, CURR SCI INDIA, V73, P1067

[4] ASYMMETRIC DIHYDROXYLATION (AD) OF N,N-DIALKYL AND N-METHOXY-N-METHYL ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED AMIDES [J].

BENNANI, YL ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1993, 34 (13) :2079-2082

[5] LIGAND-ACCELERATED CATALYSIS [J].

BERRISFORD, DJ ;

BOLM, C ;

SHARPLESS, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1059-1070

[6] N-bromoacetamide - A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins [J].

Bruncko, M ;

Schlingloff, G ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1483-1486

[7] The synthesis of enantiomerically pure (2R)-alpha-methylisoserine [J].

Cativiela, C ;

DiazdeVillegas, MD ;

Galvez, JA .

TETRAHEDRON, 1996, 52 (02) :687-694

[8] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[9] MILD AND SELECTIVE PALLADIUM(0)-CATALYZED DEALLYLATION OF ALLYLIC AMINES - ALLYLAMINE AND DIALLYLAMINE AS VERY CONVENIENT AMMONIA EQUIVALENTS FOR THE SYNTHESIS OF PRIMARY AMINES [J].

GARROHELION, F ;

MERZOUK, A ;

GUIBE, F .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :6109-6113

[10]

Hintermann T, 1997, CHIMIA, V51, P244

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