Three component synthesis of homoallylic amines. Efficient catalysis by lanthanum triflate/benzoic acid

被引:77
作者
Aspinall, HC
Bissett, JS
Greeves, N
Levin, D
机构
[1] Univ Liverpool, Donnan & Robert Robinson Labs, Dept Chem, Liverpool L69 7ZD, Merseyside, England
[2] AstraZeneca, Macclesfield SK10 2NA, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
lanthanum triflate; allylation; Bronsted acidity; Lewis acidity; imines;
D O I
10.1016/S0040-4039(01)02116-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lanthanum triflate-benzoic acid catalyses the in situ formation and allylation of various imines from aldehydes and an aromatic amine. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:323 / 325
页数:3
相关论文
共 9 条
[1]  
Akiyama T, 1998, SYNLETT, P273
[2]   Lanthanum triflate-catalysed allylation of aldehydes: crucial activation by benzoic acid [J].
Aspinall, HC ;
Bissett, JS ;
Greeves, N ;
Levin, D .
TETRAHEDRON LETTERS, 2002, 43 (02) :319-321
[3]   ASYMMETRIC ADDITION OF ORGANOLITHIUM REAGENTS TO IMINES [J].
DENMARK, SE ;
NAKAJIMA, N ;
NICAISE, OJC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8797-8798
[4]   Enantioselective synthesis of homoallylamines by nucleophilic addition of chirally modified allylboron reagents to imines [J].
Itsuno, S ;
Watanabe, K ;
Ito, K ;
ElShehawy, AA ;
Sarhan, AA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :109-110
[5]   HOMOALLYLAMINES FROM ALDIMINES AND ALLYLSTANNANES [J].
KECK, GE ;
ENHOLM, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (01) :146-147
[6]   Sc(OTf)3-catalyzed three-component reactions of aldehydes, amines and allyltributylstannane in micellar systems.: Facile synthesis of homoallylic amines in water [J].
Kobayashi, S ;
Busujima, T ;
Nagayama, S .
CHEMICAL COMMUNICATIONS, 1998, (01) :19-20
[7]   Palladium- and platinum-catalyzed addition of aldehydes and imines with allylstannanes. Chemoselective allylation of imines in the presence of aldehydes [J].
Nakamura, H ;
Iwama, H ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (28) :6641-6647
[8]   Chiral π-allylpalladium-catalyzed asymmetric allylation of imines:: Replacement of allylstannanes by allylsilanes [J].
Nakamura, K ;
Nakamura, H ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2614-2615
[9]   SELECTIVE REACTIONS USING ALLYLIC METALS [J].
YAMAMOTO, Y ;
ASAO, N .
CHEMICAL REVIEWS, 1993, 93 (06) :2207-2293