A powerful, practical and chemoselective synthesis of 2-anilinoalkanols catalyzed by Bi(TFA)3 or Bi(OTf)3 in the presence of molten TBAB

被引：66

作者：

Khodaei, MM ^{[1
]}

Khosropour, AR ^{[1
]}

Ghozati, K ^{[1
]}

机构：

[1] Razi Univ, Fac Sci, Dept Chem, Kermanshah 67149, Iran

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 17期

关键词：

ionic liquid; anilines; ring opening; epoxides; chemoselectivity; Bi(III) salts;

D O I：

10.1016/j.tetlet.2004.02.139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthesis of beta-amino alcohols by ring opening of epoxides with anilines in good to excellent yields in the presence of catalytic amounts of Bi(TFA)(3) or Bi(OTf)(3) via the use of molten tetrabutylammonium bromide (TBAB) as an ionic liquid is described. In addition, the observed chemoselectivity can be considered as a noteworthy advantage of this method. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3525 / 3529

页数：5

共 41 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2] Efficient O-trimethylsilylation of alcohols and phenols with trimethylsilyl azide catalyzed by tetrabutylammonium bromide under neat conditions [J].

Amantini, D ;

Fringuelli, F ;

Pizzo, F ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6734-6737

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

Auge, J ;

Leroy, F .

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

[4] TRICHOGIN-A-IV, AN 11-RESIDUE LIPOPEPTAIBOL FROM TRICHODERMA-LONGIBRACHIATUM [J].

AUVINGUETTE, C ;

REBUFFAT, S ;

PRIGENT, Y ;

BODO, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2170-2174

[5]

CARTER HE, 1947, J BIOL CHEM, V170, P285

[6] Calcium trifluoromethanesulfonate-catalysed aminolysis of epoxides [J].

Cepanec, I ;

Litvic, M ;

Mikuldas, H ;

Bartolincic, A ;

Vinkovic, V .

TETRAHEDRON, 2003, 59 (14) :2435-2439

[7]

Chandrasekhar S, 2000, SYNTHESIS-STUTTGART, P1817

[8] 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

[9] Ruthenium-catalyzed regioselective synthesis of 2-substituted indoles via ring-opening of epoxides by anilines [J].

Cho, CS ;

Kim, JH ;

Choi, HJ ;

Kim, TJ ;

Shim, SC .

TETRAHEDRON LETTERS, 2003, 44 (14) :2975-2977

[10]

Curini M, 2001, EUR J ORG CHEM, V2001, P4149

← 1 2 3 4 5 →