Kinetic resolution of secondary alcohols mediated by rabbit gastric lipase

被引：13

作者：

Legros, JY

Toffano, M

Drayton, SK

Rivard, M

Fiaud, JC

机构：

[1] Lab. de Synthese Asymetrique A., Inst. de Chim. Moleculaire d'Orsay, Université de Paris-Sud

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(97)00242-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Secondary benzylic alcohols were kinetically resolved by rabbit gastric lipase-mediated acylation with isopropenyl acetate. Among all the substrates tested, a high enantioselectivity was observed only for l-[2-(6-methoxy)naphthyl]ethanol 3a (E>500). Allylic alcohols 14a and 15a were also efficiently, resolved (E = 26 and 51 respectively). (C) 1997 Elsevier Science Ltd.

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页码：1915 / 1918

页数：4

相关论文

共 19 条

[1]

Arsenijevic L., 1973, ORG SYNTH, V53, P5

[2] ENZYMATIC ESTERIFICATION OF 1-FERROCENYLETHANOL - AN ALTERNATE APPROACH TO CHIRAL FERROCENYL BIS-PHOSPHINES [J].

BOAZ, NW .

TETRAHEDRON LETTERS, 1989, 30 (16) :2061-2064

[3]

CHEN CS, 1987, J AM CHEM SOC, V109, P2182

[4] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[5] STUDIES ON THE REGIOSELECTIVITY AND ENANTIOSELECTIVITY OF THE LIPASE-CATALYZED TRANSESTERIFICATION OF 1'-NAPHTHYL AND 2'-NAPHTHYL ALCOHOLS IN ORGANIC-SOLVENT [J].

FERRABOSCHI, P ;

CASATI, S ;

MANZOCCHI, A ;

SANTANIELLO, E .

TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1521-1524

[6] NEW METHOD FOR THE CLASSIFICATION OF NUCLEOPHILES IN THE PALLADIUM-CATALYZED SUBSTITUTION OF ALLYLIC ACETATES [J].

FIAUD, JC ;

LEGROS, JY .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :1907-1911

[7] KINETIC RESOLUTION OF 3-T-BUTYL AND 3-PHENYLCYCLOBUTYLIDENETHANOLS THROUGH LIPASE-CATALYZED ACYLATION WITH SUCCINIC ANHYDRIDE [J].

FIAUD, JC ;

GIL, R ;

LEGROS, JY ;

ARIBIZOUIOUECHE, L ;

KONIG, WA .

TETRAHEDRON LETTERS, 1992, 33 (46) :6967-6970

[8] CONVENIENT PRACTICAL RESOLUTION OF RACEMIC ALKYL-ARYL ALCOHOLS VIA ENZYMATIC ACYLATION WITH SUCCINIC ANHYDRIDE IN ORGANIC-SOLVENTS [J].

GUTMAN, AL ;

BRENNER, D ;

BOLTANSKI, A .

TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :839-844

[9] LIPASE-CATALYZED IRREVERSIBLE TRANSESTERIFICATION USING ENOL ESTERS - XAD-8 IMMOBILIZED LIPOPROTEIN LIPASE-CATALYZED RESOLUTION OF SECONDARY ALCOHOLS [J].

HSU, SH ;

WU, SS ;

WANG, YF ;

WONG, CH .

TETRAHEDRON LETTERS, 1990, 31 (44) :6403-6406

[10]

Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4