Catalytic Pictet-Spengler reactions using Yb(OTf)3

被引:42
作者
Manabe, K [1 ]
Nobutou, D [1 ]
Kobayashi, S [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
基金
日本学术振兴会;
关键词
catalytic reaction; Lewis acid; Pictet-Spengler reaction; Ytterbium triflate;
D O I
10.1016/j.bmc.2005.05.018
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The catalytic Pictet-Spengler reactions proceeded in high yields with high regioselectivity in the presence of a catalytic amount of Yb(OTf)(3) and a dehydrating agent at room temperature. High regioselectivities were obtained in these reactions, and it is suggested that the reactions proceeded under kinetic control. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5154 / 5158
页数:5
相关论文
共 17 条
[1]   PICTET-SPENGLER REACTIONS OF EPINEPHRINE WITH FORMALDEHYDE AND ACETALDEHYDE [J].
BATES, HA .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :4931-4935
[2]  
BRINGMANN G, COMPREHENSIVE ORGANI, V6
[3]   Asymmetric synthesis of isoquinoline alkaloids [J].
Chrzanowska, M ;
Rozwadowska, MD .
CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370
[4]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[5]   Synthesis and biological activities of the marine bryozoan alkaloids convolutamines A, C and F, and lutamides A and C [J].
Hashima, H ;
Hayashi, M ;
Kamano, Y ;
Sato, N .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (07) :1757-1766
[6]   PHENOLIC CYCLISATION .10. ISOQUINOLINE CYCLISATION UNDER BASIC CONDITIONS [J].
KAMETANI, T ;
KIGASAWA, K ;
HIIRAGI, M ;
ISHIMARU, H .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (15) :2632-&
[7]   PHENOLIC CYCLISATION .I. NOVEL SYNTHESIS OF 1-SUBSTITUTED ISOQUINOLINE AND SPIRO[CYCLOALKANE-1,1'-ISOQUINOLINE] DERIVATIVES AND ITS APPLICATION TO TOTAL SYNTHESIS OF ISOQUINOLINE ALKALOIDS [J].
KAMETANI, T ;
FUKUMOTO, K ;
AGUI, H ;
YAGI, H ;
KIGASAWA, K ;
SUGAHARA, H ;
HIIRAGI, M ;
HAYASAKA, T ;
ISHIMARU, H .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (02) :112-&
[8]   SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES AND RELATED COMPOUNDS BY PHENOLIC CYCLIZATION [J].
KAMETANI, T ;
FUKUMOTO, K ;
KIGASAWA, K ;
HIIRAGI, M ;
ISHIMARU, H .
HETEROCYCLES, 1975, 3 (04) :311-341
[9]   Rare-earth metal triflates in organic synthesis [J].
Kobayashi, S ;
Sugiura, M ;
Kitagawa, H ;
Lam, WWL .
CHEMICAL REVIEWS, 2002, 102 (06) :2227-2302
[10]   Lewis acid catalysts stable in water. Correlation between catalytic activity in water and hydrolysis constants and exchange rate constants for substitution of inner-sphere water ligands [J].
Kobayashi, S ;
Nagayama, S ;
Busujima, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8287-8288