Kinetic resolution of 1,1′-binaphthylamines via lipase-catalyzed amidation

被引：35

作者：

Aoyagi, N ^{[1
]}

Izumi, T ^{[1
]}

机构：

[1] Yamagata Univ, Grad Sch Sci & Engn, Dept Chem & Chem Engn, Yonezawa, Yamagata 9928510, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 32期

关键词：

binaphthyl; Suzuki cross-coupling; enzymes; amidation;

D O I：

10.1016/S0040-4039(02)01162-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lipase-catalyzed amidation of 2-(2-aminoethyl)-1,1'-binaplithyl (+/-)-3 gave optically active 2-[2-(acylamino)ethyl]-1,1'binaphthyls (R)-6a-c with high enantiomeric excess. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5529 / 5531

页数：3

共 23 条

[1] SYNTHESIS OF OPTICALLY-ACTIVE 2,2'-DIHALO-1,1'-BINAPHTHYLS VIA STABLE DIAZONIUM SALTS [J].

BROWN, KJ ;

BERRY, MS ;

MURDOCH, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4345-4349

[2]

Carrea G, 2000, ANGEW CHEM INT EDIT, V39, P2226

[3] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[4] Lipase-catalyzed synthesis of chiral amides. A systematic study of the variables that control the synthesis [J].

de Castro, MS ;

Gago, JVS .

TETRAHEDRON, 1998, 54 (12) :2877-2892

[5]

FABER K, 1992, SYNTHESIS-STUTTGART, P895

[6] SYNTHESIS OF OPTICALLY-ACTIVE AMIDES FROM BETA-FURYL AND BETA-PHENYL ESTERS BY WAY OF ENZYMATIC AMINOLYSIS [J].

GOTOR, V ;

MENENDEZ, E ;

MOULOUNGUI, Z ;

GASET, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (20) :2453-2456

[7] Non-conventional hydrolase chemistry: Amide and carbamate bond formation catalyzed by lipases [J].

Gotor, V .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (10) :2189-2197

[8] ENZYMATIC AMINOLYSIS AND TRANSAMIDATION REACTIONS [J].

GOTOR, V ;

BRIEVA, R ;

GONZALEZ, C ;

REBOLLEDO, F .

TETRAHEDRON, 1991, 47 (44) :9207-9214

[9] ENANTIOSELECTIVE REDUCTION OF KETONES WITH REAGENTS FROM LITHIUM ALUMINUM-HYDRIDE AND AXIALLY CHIRAL 2,2'-DIAMINO-1,1'-BINAPHTHYLS [J].

KABUTO, K ;

YOSHIDA, T ;

YAMAGUCHI, S ;

MIYANO, S ;

HASHIMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :3013-3015

[10] ENZYMATIC RESOLUTION OF RACEMIC AMINES - CRUCIAL ROLE OF THE SOLVENT [J].

KITAGUCHI, H ;

FITZPATRICK, PA ;

HUBER, JE ;

KLIBANOV, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :3094-3095

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