Catalytic asymmetric Pictet-Spengler reaction

被引:416
作者
Seayad, J [1 ]
Seayad, AM [1 ]
List, B [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
D O I
10.1021/ja057444l
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalytic asymmetric Pictet-Spengler reaction has been developed, wherein treating substituted tryptamines with an aldehyde in the presence of a catalytic amount of a chiral phosphoric acid provides the corresponding tetrahydro-β-carboline derivatives in high yields and enantiomeric excesses. The reaction works well with both aliphatic and aromatic aldehydes. Copyright © 2006 American Chemical Society.
引用
收藏
页码:1086 / 1087
页数:2
相关论文
共 31 条
[1]   Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].
Akiyama, T ;
Saitoh, Y ;
Morita, H ;
Fuchibe, K .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526
[2]   Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].
Akiyama, T ;
Morita, H ;
Itoh, J ;
Fuchibe, K .
ORGANIC LETTERS, 2005, 7 (13) :2583-2585
[3]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[4]  
[Anonymous], [No title captured]
[5]   Asymmetric synthesis of isoquinoline alkaloids [J].
Chrzanowska, M ;
Rozwadowska, MD .
CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370
[6]   Enantiospecific formation of trans 1,3-disubstituted tetrahydro-beta-carbolines by the Pictet-Spengler reaction and conversion of cis diastereomers into their trans counterparts by scission of the C-1/N-2 bond [J].
Cox, ED ;
Hamaker, LK ;
Li, J ;
Yu, P ;
Czerwinski, KM ;
Deng, L ;
Bennett, DW ;
Cook, JM ;
Watson, WH ;
Krawiec, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :44-61
[7]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[8]   ENANTIOSELECTIVE SYNTHESIS OF ISOQUINOLINE ALKALOIDS [J].
CZARNOCKI, Z ;
MACLEAN, DB ;
SZAREK, WA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (11) :2205-2210
[9]   ENANTIOSELECTIVE SYNTHESIS OF 1-SUBSTITUTED TETRAHYDROISOQUINOLINE-1-CARBOXYLIC ACIDS [J].
CZARNOCKI, Z ;
SUH, D ;
MACLEAN, DB ;
HULTIN, PG ;
SZAREK, WA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (05) :1555-1561
[10]   Pictet-Spengler reaction of biogenic amines with (2R)-N-glyoxyloylbornane-10,2-sultam. Enantioselective synthesis of (S)-(+)-N-methylcalycotomine [J].
Czarnocki, Z ;
Mieczkowski, JB ;
Kiegiel, J ;
Arazny, Z .
TETRAHEDRON-ASYMMETRY, 1995, 6 (12) :2899-2902