Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group

被引：24

作者：

Jiang, Minghui ^{[1
]}

Feng, Lifei ^{[1
]}

Feng, Juanjuan ^{[1
]}

Jiao, Peng ^{[1
]}

机构：

[1] Beijing Normal Univ, Key Lab Radiopharmaceut, Coll Chem, Beijing 100875, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 09期

基金：

中国国家自然科学基金;

关键词：

1,3-DIPOLAR CYCLOADDITION; 1-ARYL-SUBSTITUTED NITROALKANES; ORGANIC-SYNTHESIS; MICHAEL ADDITION; NITRILE OXIDES; ACID; ISOXAZOLINES; ROUTES; ESTERS;

D O I：

10.1021/acs.orglett.7b00558

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an alpha-ary] group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey's oxazaborolidine catalyst. Specifically, the TIPS nitronate with an alpha-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.

引用

页码：2210 / 2213

页数：4

共 37 条

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[2] Harnessing the ambiphilicity of silyl nitronates in a catalytic asymmetric approach to aliphatic β3-amino acids
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[4] ASYMMETRIC SILYL NITRONATE CYCLOADDITIONS WITH BORNANE-10,2-SULTAM DERIVATIVES
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[10] Deracemization of α-Aryl Hydrocoumarins via Catalytic Asymmetric Protonation of Ketene Dithioacetals
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