Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic and direct α-benzoyloxylation of aldehydes

被引：56

作者：

Gotoh, Hiroaki ^{[1
]}

Hayashi, Yujiro ^{[1
,2
]}

机构：

[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan

[2] Tokyo Univ Sci, Res Inst Sci & Technol, Shinjuku Ku, Tokyo 1628601, Japan

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 21期

关键词：

3+3 CYCLOADDITION REACTION; DIELS-ALDER REACTIONS; MICHAEL REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE FORMATION; STEREOCENTERS; ORGANOCATALYSIS; AMINOXYLATION; CHEMISTRY; KETONES;

D O I：

10.1039/b902287b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diphenylprolinol silyl ether was found to promote asymmetric, catalytic and direct alpha-benzoyloxylation of aldehydes with benzoyl peroxide to afford oxidized products in good yields with excellent enantioselectivity.

引用

页码：3083 / 3085

页数：3

共 45 条

[1]

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

[2] 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

[3] The direct amino acid-catalyzed asymmetric incorporation of molecular oxygen to organic compounds [J].

Córdova, A ;

Sundén, H ;

Engqvist, M ;

Ibrahem, I ;

Casas, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :8914-8915

[4]

Dalko P.I., 2007, ENANTIOSELECTIVE ORG

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

Dalko, PI ;

Moisan, L .

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

[6] Asymmetric organocatalysis: From infancy to adolescence [J].

Dondoni, Alessandro ;

Massi, Alessandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4638-4660

[7] Control of four stereocentres in a triple cascade organocatalytic reaction [J].

Enders, Dieter ;

Hüettl, Matthias R. M. ;

Grondal, Christoph ;

Raabe, Gerhard .

NATURE, 2006, 441 (7095) :861-863

[8] Organocatalytic enantioselective one-pot synthesis and application of substituted 1,4-dihydropyridines - Hantzsch Ester analogues [J].

Franke, Patrick T. ;

Johansen, Rasmus L. ;

Bertelsen, Soren ;

Jorgensen, Karl Anker .

CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (02) :216-224

[9] Enantioselective organocatalysis [J].

Gaunt, Matthew J. ;

Johansson, Carin C. C. ;

McNally, Andy ;

Vo, Ngoc T. .

DRUG DISCOVERY TODAY, 2007, 12 (1-2) :8-27

[10] Diphenylprolinol silyl ether as catalyst of an asymmetric, catalytic, and direct Michael reaction of nitroalkanes with α,β-unsaturated aldehydes [J].

Gotoh, Hiroaki ;

Ishikawa, Hayato ;

Hayashi, Yujilro .

ORGANIC LETTERS, 2007, 9 (25) :5307-5309

← 1 2 3 4 5 →