PRACTICAL ASYMMETRIC SYNTHESES OF ALL 4 2,3-METHANOLEUCINE STEREOISOMERS

被引：30

作者：

BURGESS, K

LI, W

机构：

[1] Department of Chemistry Texas A, M University College Station

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 16期

关键词：

CONFORMATIONALLY CONSTRAINED; CYCLOPROPANE; AMINO ACID;

D O I：

10.1016/0040-4039(95)00382-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

All four stereoisomers of the 2,3-methanoamino acids BOC-E-cyclo-Leu and BOC-Z-cyclo-Leu were prepared from the optically active diol 4 (and its enantiomer) derived from valine, The challenges associated with introducing protected amine functionalities cis to the side chain were overcome by using the vinylogous malonate synthon, dimethyl gluconate.

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页码：2725 / 2728

页数：4

相关论文

共 15 条

[1] ASYMMETRIC SYNTHESES OF PROTECTED DERIVATIVES OF ORNITHINE- -METHANOLOGS AND ARGININE-2,3-METHANOLOGS [J].

BURGESS, K ;

HO, KK .

TETRAHEDRON LETTERS, 1992, 33 (39) :5677-5680

[2] ASYMMETRIC SYNTHESES OF ALL 4 STEREOISOMERS OF 2,3-METHANOMETHIONINE [J].

BURGESS, K ;

HO, KK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5931-5936

[3] ASYMMETRIC SYNTHESES OF PROTECTED DERIVATIVES OF CARNOSADINE AND ITS STEREOISOMERS AS CONFORMATIONALLY CONSTRAINED SURROGATES FOR ARGININE [J].

BURGESS, K ;

LIM, D ;

HO, KK ;

KE, CY .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :2179-2185

[4] A GAMMA-TURN STRUCTURE INDUCED BY 2S,3S-2,3-METHANOMETHIONINE [J].

BURGESS, K ;

HO, KK ;

PETTITT, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :799-800

[5] SYNTHESIS OF A VALUABLE CYCLOPROPYL CHIRON FOR PREPARATIONS OF 2,3-METHANOAMINO ACIDS [J].

BURGESS, K ;

HO, KK ;

KE, CY .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3767-3768

[6] A REAGENT FOR DETERMINING OPTICAL PURITIES OF DIOLS BY FORMATION OF DIASTEREOMERIC ARYLBORONATE ESTERS [J].

BURGESS, K ;

PORTE, AM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (11) :1182-1184

[7]

BURGESS K, 1994, UNPUB J AM CHEM SOC

[8]

BURGESS K, 1994, IN PRESS J AM CHEM S

[9]

BURGESS K, 1994, SYNLETT, V8, P575

[10] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938