Thermal effects in the organocatalytic asymmetric α-amination of disubstituted aldehydes with azodicarboxylates:: A high-temperature organocatalysis

被引：52

作者：

Baumann, Thomas ^{[1
]}

Baechle, Michael ^{[1
]}

Hartmann, Caroline ^{[1
]}

Braese, Stefan ^{[1
]}

机构：

[1] Univ Karlsruhe TH, Inst Organ Chem, D-76131 Karlsruhe, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 13期

关键词：

microwave; organocatalysis; alpha-amination; amino aldehydes;

D O I：

10.1002/ejoc.200701167

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This article describes the thermally accelerated organocatalytic alpha-amination of disubstituted aldehydes with azodicarboxylates under microwave conditions. Compared to the results previously obtained at room temperature, both yield and enantioselectivity could be significantly increased. Employing microwave irradiation resulted in a considerably reduced reaction time. Therefore, this improved protocol allows the fast and efficient synthesis of alpha,alpha-disubstituted amino aldehydes and provided the best results for the alpha-amination of disubstituted aldehydes to date. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：2207 / 2212

页数：6

共 78 条

[1] Electrophilic amination of racemic and non-racemic allenyltitaniums.: One-pot synthesis of α-hydrazinoalkynes from propargylic alcohol derivatives [J].

An, DK ;

Hirakawa, K ;

Okamoto, S ;

Sato, F .

TETRAHEDRON LETTERS, 1999, 40 (19) :3737-3740

[2] AMINATIONS WITH OXAZIRIDINES - SYNTHESES OF ARYL-HYDRAZINES AND HETARYL-HYDRAZINES [J].

ANDREAE, S ;

SCHMITZ, E .

HETEROCYCLES, 1994, 37 (01) :379-386

[3] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN ;

Martin, HJ ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479

[4] A short synthesis of (S)-2-(diphenylmethyl)pyrrolidine, a chiral solvating agent for NMR analysis [J].

Bailey, DJ ;

OHagan, D ;

Tavasli, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :149-153

[5] Catalytic enantioselective conjugate addition of indoles to simple α,β-unsaturated ketones [J].

Bandini, M ;

Fagioli, M ;

Melchiorre, P ;

Melloni, A ;

Umani-Ronchi, A .

TETRAHEDRON LETTERS, 2003, 44 (31) :5843-5846

[6]

BARTON D, 1979, COMPREHENSIVE ORG 23, V5, P177

[7]

BARTON D, 1979, COMPREHENSIVE ORG 28, V5, P867

[8]

BARTON D, 1979, COMPREHENSIVE ORG 30, V5, P1043

[9]

BARTON D, 1979, COMPREHENSIVE ORG 22, V5, P21

[10] The proline-catalyzed asymmetric Amination of branched aldehydes [J].

Baumann, Thomas ;

Vogt, Henning ;

Braese, Stefan .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (02) :266-282

← 1 2 3 4 5 6 7 8 →