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

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 12期

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

页码：2193 / 2198

页数：6

共 50 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
Ahrendt, KA
Borths, CJ
MacMillan, DWC
[J]. 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
AMOROSO, R
CARDILLO, G
SABATINO, P
TOMASINI, C
TRERE, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) : 5615 - 5619
[3] BALENOVIC K, 1957, CROAT CHEM ACTA, V29, P153
[4] Enantioselective organocatalytic amine conjugate addition
Chen, Young K.
Yoshida, Masanori
MacMillan, David W. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) : 9328 - 9329
[5] The direct catalytic asymmetric cross-Mannich reaction:: A highly enantioselective route to 3-amino alcohols and α-amino acid derivatives
Córdova, A
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) : 1987 - 1997
[6] anti-selective SMP-catalyzed direct asymmetric Mannich-type reactions:: synthesis of functionalized amino acid derivatives
Córdova, A
Barbas, CF
[J]. TETRAHEDRON LETTERS, 2002, 43 (43) : 7749 - 7752
[7] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives
Córdova, A
Watanabe, S
Tanaka, F
Notz, W
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1866 - 1867
[8] LITHIUM (ALPHA-METHYLBENZYL)ALLYLAMIDE - A DIFFERENTIALLY PROTECTED CHIRAL AMMONIA EQUIVALENT FOR THE ASYMMETRIC-SYNTHESIS OF BETA-AMINO ACIDS AND BETA-LACTAMS
DAVIES, SG
FENWICK, DR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) : 1109 - 1110
[9] Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates
Doi, H
Sakai, T
Iguchi, M
Yamada, K
Tomioka, K
[J]. 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
Dumas, F
Mezrhab, B
dAngelo, J
Riche, C
Chiaroni, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) : 2293 - 2304

← 1 2 3 4 5 →