An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichloride

被引：147

作者：

Ollevier, T ^{[1
]}

Lavie-Compin, G ^{[1
]}

机构：

[1] Univ Laval, Dept Chim, Quebec City, PQ G1K 7P4, Canada

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 44期

基金：

加拿大自然科学与工程研究理事会;

关键词：

bismuth; bismuth(III) chloride; epoxide; aromatic amine; beta-amino alcohol; catalysis;

D O I：

10.1016/S0040-4039(02)01896-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe here the nucleophilic opening of epoxides with aromatic amines in the presence of a catalytic amount of BiCl3. The mild reaction conditions and the low toxicity of bismuth salts make this procedure particularly attractive for the synthesis of beta-amino alcohols. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7891 / 7893

页数：3

共 40 条

[1] Lithium trifluoromethanesulfonate-catalysed aminolysis of oxiranes [J].

Auge, J ;

Leroy, F .

TETRAHEDRON LETTERS, 1996, 37 (43) :7715-7716

[2] A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate [J].

Bhatia, KA ;

Eash, KJ ;

Leonard, NM ;

Oswald, MC ;

Mohan, RS .

TETRAHEDRON LETTERS, 2001, 42 (46) :8129-8132

[3] A simple and efficient chemoselective method for the catalytic deprotection of acetals and ketals using bismuth triflate [J].

Carrigan, MD ;

Sarapa, D ;

Smith, RC ;

Wieland, LC ;

Mohan, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :1027-1030

[4] An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate [J].

Carrigan, MD ;

Eash, KJ ;

Oswald, MC ;

Mohan, RS .

TETRAHEDRON LETTERS, 2001, 42 (46) :8133-8135

[5]

Chandrasekhar S, 2000, SYNTHESIS-STUTTGART, P1817

[6] REGIOALTERNATING SELECTIVITY IN THE METAL SALT CATALYZED AMINOLYSIS OF STYRENE OXIDE [J].

CHINI, M ;

CROTTI, P ;

MACCHIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5939-5942

[7] LANTHANIDE(III) TRIFLUOROMETHANESULFONATES AS EXTRAORDINARILY EFFECTIVE NEW CATALYSTS FOR THE AMINOLYSIS OF 1,2-EPOXIDES [J].

CHINI, M ;

CROTTI, P ;

FAVERO, L ;

MACCHIA, F ;

PINESCHI, M .

TETRAHEDRON LETTERS, 1994, 35 (03) :433-436

[8] Solution-phase synthesis of a beta-amino alcohol combinatorial library [J].

Chng, BL ;

Ganesan, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (12) :1511-1514

[9] Facile ring opening of oxiranes with aromatic amines in fluoro alcohols [J].

Das, U ;

Crousse, B ;

Kesavan, V ;

Bonnet-Delpon, D ;

Bégué, JP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6749-6751

[10] Surprising catalytic activity of bismuth (III) triflate in the Friedel-Crafts acylation reaction [J].

Desmurs, JR ;

Labrouillere, M ;

LeRoux, C ;

Gaspard, H ;

Laporterie, A ;

Dubac, J .

TETRAHEDRON LETTERS, 1997, 38 (51) :8871-8874

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