Direct organocatalytic asymmetric α-oxidation of ketones with iodosobenzene and N-sulfonyloxaziridines

被引：46

作者：

Engqvist, M ^{[1
]}

Casas, J ^{[1
]}

Sundén, H ^{[1
]}

Ibrahem, I ^{[1
]}

Córdova, A ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 12期

关键词：

D O I：

10.1016/j.tetlet.2005.01.167

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The novel, direct amino acid-catalyzed alpha-oxidation of ketones with iodosobenzene and N-sulfonyloxaziridines is presented. A screen of several synthetically common oxidants revealed that iodosobenzene and N-sulfonyloxaziridines act as electrophiles in the direct organocatalytic asymmetric alpha-hydroxylation of ketones. The direct proline-catalyzed asymmetric alpha-oxidation of ketones with iodosobenzene yielded the corresponding alpha-hydroxylated ketones with up to 77% ee. Furthermore, several amino acid derivatives catalyze the stereoselective alpha-oxidation of ketones with N-sulfonyloxaziridines. For example, the direct diamine-catalyzed enantioselective alpha-hydroxylation of ketones with N-sulfonyloxaziridines furnished the corresponding alpha-hydroxylated products in moderate yield with up to 63% ee. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2053 / 2057

页数：5

共 52 条

[1] Epoxidation of alkenes by amine catalyst precursors: Implication of aminium ion and radical cation intermediates [J].

Adamo, MFA ;

Aggarwal, VK ;

Sage, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8317-8318

[2] Amine-catalyzed epoxidation of alkenes: A new mechanism for the activation of oxone [J].

Armstrong, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1460-1462

[3] Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones [J].

Bogevig, A ;

Sundén, H ;

Córdova, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1109-1112

[4]

Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO

[5]

2-Y

[6] THE STEREOSPECIFIC SYNTHESIS OF A NEW CHIRAL OXAZIRIDINIUM SALT [J].

BOHE, L ;

HANQUET, G ;

LUSINCHI, M ;

LUSINCHI, X .

TETRAHEDRON LETTERS, 1993, 34 (45) :7271-7274

[7] The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].

Brown, SP ;

Brochu, MP ;

Sinz, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809

[8] Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes [J].

Casas, J ;

Sundén, H ;

Córdova, A .

TETRAHEDRON LETTERS, 2004, 45 (32) :6117-6119

[9] Direct organocatalytic ring-opening polymerizations of lactones [J].

Casas, J ;

Persson, PV ;

Iversen, T ;

Córdova, A .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1087-1089

[10] Origins of selectivities in proline-catalyzed α-aminoxylations [J].

Cheong, PHY ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) :13912-13913

← 1 2 3 4 5 6 →