High substrate/catalyst organocatalysis by a chiral bronsted acid for an enantioselective aza-ene-type reaction

被引：238

作者：

Terada, M ^{[1
]}

Machioka, K ^{[1
]}

Sorimachi, K ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 14期

关键词：

asymmetric synthesis; Bronsted acids; ene reaction; organocatalysis; phosphoric acid;

D O I：

10.1002/anie.200503477

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Lowering the load: A very small amount of a binaphthol-derived monophosphoric acid organocatalyst accelerates an azaene-type reaction of N-benzoylimines with enecarbamates to provide β-aminoimines with high enantiomeric purity. This catalysis with a high substrate/catalyst(S/ C) ratio provides a practical route to 1,3-diamine derivatives of synthetic and biological importance. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2254 / 2257

页数：4

共 56 条

[1] 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

[2] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].

Akiyama, T ;

Saitoh, Y ;

Morita, H ;

Fuchibe, K .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526

[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]

Akiyama T., 2004, ANGEW CHEM, V116, P1592, DOI DOI 10.1002/ANGE.200353240

[6]

[Anonymous], 2002, MACROMOL CHEM PHYS

[7]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[8]

Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[9] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[10] Diastereoselective alkylations of chiral, phosphorus-stabilized carbanions:: N-alkyl substituent effects in P-alkyl-1,3,2-diazaphosphorinane 2-oxides [J].

Denmark, SE ;

Kim, JH .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2000, 78 (06) :673-688

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