Enantioselective organocatalytic conjugate addition of amines to α,β-unsaturated aldehydes:: one-pot asymmetric synthesis of β-amino acids and 1,3-diamines

被引:97
作者
Vesely, Jan [1 ]
Ibrahem, Ismail [1 ]
Rios, Ramon [1 ]
Zhao, Gui-Ling [1 ]
Xu, Yongmei [1 ]
Cordova, Armando [1 ]
机构
[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
关键词
CROSS-MANNICH REACTION; CHIRAL AMMONIA EQUIVALENT; DIELS-ALDER REACTIONS; AZA-MICHAEL REACTION; ALPHA-AMINO; DERIVATIVES; CATALYSIS; 3-COMPONENT; CYCLIZATION; ENANTIOMER;
D O I
10.1016/j.tetlet.2007.01.093
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Organocatalytic asymmetric amine conjugate additions to alpha, beta-unsaturated aldehydes catalyzed by protected diarylprolinols are presented. The reactions proceed with high enantioselectivity and result in Cbz or Boc protected beta-amino aldehydes, gamma-amino alcohols, beta-amino acids and 1,3-diamines with typically 82-99% ee. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2193 / 2198
页数:6
相关论文
共 50 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]   LEWIS ACID-PROMOTED 1,4-ADDITION TO CHIRAL IMIDE DERIVATIVES IN THE SYNTHESIS OF BETA-AMINO ACIDS [J].
AMOROSO, R ;
CARDILLO, G ;
SABATINO, P ;
TOMASINI, C ;
TRERE, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5615-5619
[3]  
BALENOVIC K, 1957, CROAT CHEM ACTA, V29, P153
[4]   Enantioselective organocatalytic amine conjugate addition [J].
Chen, Young K. ;
Yoshida, Masanori ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9328-9329
[6]   anti-selective SMP-catalyzed direct asymmetric Mannich-type reactions:: synthesis of functionalized amino acid derivatives [J].
Córdova, A ;
Barbas, CF .
TETRAHEDRON LETTERS, 2002, 43 (43) :7749-7752
[7]   A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].
Córdova, A ;
Watanabe, S ;
Tanaka, F ;
Notz, W ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867
[9]   Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates [J].
Doi, H ;
Sakai, T ;
Iguchi, M ;
Yamada, K ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2886-2887
[10]   Investigating the pi-facial discrimination phenomenon in the conjugate addition of amines to chiral crotonates: A convenient basis for the rational design of chiral auxiliaries [J].
Dumas, F ;
Mezrhab, B ;
dAngelo, J ;
Riche, C ;
Chiaroni, A .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2293-2304