Acyclic β-amino acid catalyzed asymmetric anti-selective Mannich-type reactions

被引:53
作者
Dziedzic, Pawel [1 ]
Cordova, Armando [1 ]
机构
[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden
关键词
D O I
10.1016/j.tetasy.2007.04.024
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The ability of a primary amine containing acyclic beta(3)-amino acids to catalyze direct asymmetric anti-selective Mannich-type reactions is presented. The reactions are generally highly diastereo- and enantioselective to give the corresponding Mannich products with up to >19:1 dr (anti/syn) and 88-99% ee. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1033 / 1037
页数:5
相关论文
共 79 条
[1]   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
[2]   Stereocontrolled asymmetric synthesis of α-hydroxy-β-amino acids.: A stereodivergent approach [J].
Aoyagi, Y ;
Jain, RP ;
Williams, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3472-3477
[3]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[4]  
2-E
[5]   CONTRIBUTION TO ASYMMETRIC SYNTHESIS OF BICYCLIC COMPOUNDS CATALYZED BY OPTICALLY-ACTIVE AMINO-ACIDS - SYNTHESIS OF (S)-2-PYRROLIDINEPROPIONIC ACID AND (R)-4-AMINO-5-PHENYLVALERIC ACID [J].
BUCHSCHACHER, P ;
CASSAL, JM ;
FURST, A ;
MEIER, W .
HELVETICA CHIMICA ACTA, 1977, 60 (08) :2747-2755
[6]   Enantioselective organocatalytic aminomethylation of aldehydes:: A role for ionic interactions and efficient access to β2-amino acids [J].
Chi, Yonggui ;
Gellman, Samuel H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6804-6805
[7]   Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions [J].
Cobb, AJA ;
Shaw, DM ;
Longbottom, DA ;
Gold, JB ;
Ley, SV .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :84-96
[8]   5-pyrrolidin-2-yltetrazole: A new, catalytic, more soluble alternative to proline in an organocatalytic asymmetric Mannich-type reaction [J].
Cobb, AJA ;
Shaw, DM ;
Ley, SV .
SYNLETT, 2004, (03) :558-560
[9]   Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides (vol 12, pg 5383, 2006) [J].
Cordova, A. ;
Zou, W. ;
Dziedzic, R. ;
Ibrahem, I. ;
Reyes, E. ;
Xu, Y. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (20) :5175-5175