Highly efficient three-component synthesis of protected homoallylic amines by bismuth triflate-catalyzed allylation of aldimines

被引：82

作者：

Ollevier, T ^{[1
]}

Ba, T ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 50期

基金：

加拿大自然科学与工程研究理事会;

关键词：

bismuth triflate; allylation; aldimines; allylsilane;

D O I：

10.1016/j.tetlet.2003.09.221

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bismuth triflate catalyzes the allylation of a variety of in situ generated protected aldimines using aldehydes, primary carbamates, and allyltrimethylsilane in a three-component reaction. The reaction proceeds rapidly and affords the corresponding protected homoallylic amine in good yield (up to 86%). Scope and limitations of the aldehyde and carbamate components are reported. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9003 / 9005

页数：3

共 37 条

[1] Tin(II) chloride mediated allylation of aldimines generated in situ with allylstannane in water [J].

Akiyama, T ;

Onuma, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (09) :1157-1158

[2] Three component synthesis of homoallylic amines. Efficient catalysis by lanthanum triflate/benzoic acid [J].

Aspinall, HC ;

Bissett, JS ;

Greeves, N ;

Levin, D .

TETRAHEDRON LETTERS, 2002, 43 (02) :323-325

[3] 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

[4] 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

[5] Highly efficient allylation of aldehydes and three-component synthesis of homoallylamines using bismuth triflate catalyst [J].

Choudary, BM ;

Chidara, S ;

Sekhar, CVR .

SYNLETT, 2002, (10) :1694-1696

[6] 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

[7] A simple chemoselective method for the deprotection of acetals and ketals using bismuth nitrate pentahydrate [J].

Eash, KJ ;

Pulia, MS ;

Wieland, LC ;

Mohan, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8399-8401

[8] Diels-Alder reaction catalyzed by bismuth(II) salts [J].

Garrigues, B ;

Oussaid, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 585 (02) :253-255

[9]

Hiemstra H., 1991, COMPREHENSIVE ORGANI, V2, P1047

[10] Chiral oxime ethers in asymmetric synthesis.: Part 4.: Asymmetric synthesis of N-protected amines and β-amino acids by the addition of organometallic reagents to ROPHy/SOPHy-derived aldoximes [J].

Hunt, JCA ;

Lloyd, C ;

Moody, CJ ;

Slawin, AMZ ;

Takle, AK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (23) :3443-3454

← 1 2 3 4 →