Direct catalytic asymmetric three-component Kabachnik-Fields reaction

被引：152

作者：

Cheng, Xu ^{[1
]}

Goddard, Richard ^{[1
]}

Buth, Gernot ^{[2
]}

List, Benjamin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

[2] Forschungszentrum Karlsruhe, ISS, D-76021 Karlsruhe, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 27期

关键词：

asymmetric catalysis; chiral phosphoric acid; dynamic kinetic resolution; hydrophosphonylation; organocatalysis;

D O I：

10.1002/anie.200801173

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) As mimics of α-amino acids, α-amino phosphonates have great promise as antibacterial and anti-HIV agents as well as protease inhibitors. Racemic α-branched aldehydes react, in the presence the new chiral phosphoric acid catalyst 1, directly with p-anisidine (PMPNH2) and a phosphite to furnish β-branched α-amino phosphonates highly diastereoselectively and enantioselectively. Anth = anthracenyl. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5079 / 5081

页数：3

共 73 条

[1] ADAIR G, 2008, ALDRICHIMIC IN PRESS
[2] Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity
Akiyama, T
Tamura, Y
Itoh, J
Morita, H
Fuchibe, K
[J]. SYNLETT, 2006, (01) : 141 - 143
[3] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates
Akiyama, T
Morita, H
Itoh, J
Fuchibe, K
[J]. ORGANIC LETTERS, 2005, 7 (13) : 2583 - 2585
[4] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
Akiyama, T
Itoh, J
Yokota, K
Fuchibe, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
[5] Akiyama T., 2006, Patent, Patent No. [EP1623971A1, 1623971]
[6] Akiyama T., 2004, ANGEW CHEM, V116, P1592, DOI DOI 10.1002/ANGE.200353240
[7] Stronger bronsted acids
Akiyama, Takahiko
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
[8] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction
Akiyama, Takahiko
Morita, Hisashi
Fuchibe, Kohei
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) : 13070 - 13071
[9] PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS
ALLEN, JG
ATHERTON, FR
HALL, MJ
HASSALL, CH
HOLMES, SW
LAMBERT, RW
NISBET, LJ
RINGROSE, PS
[J]. NATURE, 1978, 272 (5648) : 56 - 58
[10] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND
ALLEN, MC
FUHRER, W
TUCK, B
WADE, R
WOOD, JM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) : 1652 - 1661

← 1 2 3 4 5 6 7 8 →