Pentanidium-Catalyzed Enantioselective α-Hydroxylation of Oxindoles Using Molecular Oxygen

被引：140

作者：

Yang, Yuanyong ^{[2
]}

Moinodeen, Farhana ^{[2
]}

Chin, Willy ^{[2
]}

Ma, Ting ^{[2
]}

Jiang, Zhiyong ^{[1
]}

Tan, Choon-Hong ^{[1
,3
]}

机构：

[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China

[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[3] Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 18期

基金：

中国国家自然科学基金;

关键词：

PHASE-TRANSFER CATALYSTS; QUATERNARY AMMONIUM-IONS; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; KETONES; OXIDATION; ESTERS;

D O I：

10.1021/ol302030v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pentanidium-catalyzed alpha-hydroxylation of 3-substituted-2-oxindoles using molecular oxygen has been developed with good yields and enantioselectivities. This reaction does not require an additional reductant such as triethyl phosphite, which was typically added to reduce the peroxide intermediate. The reaction was demonstrated to consist of two-steps: an enantioselective formation of hydroperoxide oxindole and a kinetic resolution of the hydroperoxicle oxindole via reduction with enolates generated from the oxindoles.

引用

页码：4762 / 4765

页数：4

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