An enantioselective chiral bronsted acid catalyzed imino-azaenamine reaction

被引:101
作者
Rueping, Magnus
Sugiono, Erli
Theissmann, Thomas
Kuenkel, Alexander
Koeckritz, Angela
Pews-Davtyan, Anahit
Nemati, Navid
Beller, Matthias
机构
[1] Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60438 Frankfurt, Germany
[2] Leibniz Inst Catalysis, D-18059 Rostock, Germany
关键词
D O I
10.1021/ol063112p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective Bronsted acid catalyzed addition of methyleneaminopyrrolidine to N-Boc imines has been achieved in the presence of chiral phosphoric acids derived from 3,3'-di(phenanthryl)-H8-BINOL. The corresponding aminohydrazones have been isolated in good yields with enantiomeric excesses up to 90%.
引用
收藏
页码:1065 / 1068
页数:4
相关论文
共 45 条
[1]   Asymmetric sulfur ylide mediated aziridination: Application in the synthesis of the side chain of taxol [J].
Aggarwal, VK ;
Vasse, JL .
ORGANIC LETTERS, 2003, 5 (21) :3987-3990
[2]   Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity [J].
Akiyama, T ;
Tamura, Y ;
Itoh, J ;
Morita, H ;
Fuchibe, K .
SYNLETT, 2006, (01) :141-143
[3]   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
[4]   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
[5]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[6]  
[Anonymous], 2002, MACROMOL CHEM PHYS
[7]   Protonated chiral catalysts: Versatile tools for asymmetric synthesis [J].
Bolm, C ;
Rantanen, T ;
Schiffers, I ;
Zani, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1758-1763
[8]   Highly enantioselective organocatalytic Biginelli reaction [J].
Chen, Xiao-Hua ;
Xu, Xiao-Ying ;
Liu, Hua ;
Cun, Lin-Feng ;
Gong, Liu-Zhu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14802-14803
[9]   Asymmetric synthesis of γ-cyano silyl enol ethers [J].
Díez, E ;
Fernández, R ;
Martín-Zamora, E ;
Pareja, C ;
Prieto, A ;
Lassaletta, JM .
TETRAHEDRON-ASYMMETRY, 1999, 10 (06) :1145-1151
[10]   Direct synthesis of dithioketals from N,N-dialkylhydrazones [J].
Diez, E ;
Lopez, AM ;
Pareja, C ;
Martin, E ;
Fernandez, R ;
Lassaletta, JM .
TETRAHEDRON LETTERS, 1998, 39 (43) :7955-7958