Diastereoselective Synthesis of 4-Hydroxytetralones via a Cascade Stetter-Aldol Reaction Catalyzed by N-Heterocyclic Carbenes

被引：46

作者：

Sun, Fang-Gang ^{[1
]}

Huang, Xue-Liang ^{[1
]}

Ye, Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 01期

基金：

美国国家科学基金会;

关键词：

ACTIVATED DOUBLE-BONDS; KINETIC RESOLUTION; DOMINO REACTIONS; ORGANOCATALYSIS; OXIDATION; ALDEHYDES; KETENES;

D O I：

10.1021/jo902376t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cascade Stetter-aldol reaction of phthalaldehyde and Michael acceptors catalyzed by N-heterocyclic carbenes was developed. The corresponding 3-substituted-4-hydroxytetralones were obtained in moderate to good yields with good trans-selectivities. On the contrary, the separated Stetter reaction followed by aldol reaction gave 3-substituted-4-hydroxytetralones with good cis-selectivity. Oxidation or dehydration of the resulted 4-hydroxytetralone gave the corresponding naphthalenediol or naphthol derivative, respectively, in good yield.

引用

页码：273 / 276

页数：4

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