Enantiodifferentiating endo-Selective Oxylactonization of ortho-Alk-1-enylbenzoate with a Lactate-Derived Aryl-λ3-Iodane

被引：164

作者：

Fujita, Morifumi ^{[1
]}

Yoshida, Yasushi ^{[1
]}

Miyata, Kazuyuki ^{[1
]}

Wakisaka, Akihiro ^{[1
]}

Sugimura, Takashi ^{[1
]}

机构：

[1] Univ Hyogo, Grad Sch Mat Sci, Kamigori, Hyogo 6781297, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 39期

关键词：

asymmetric synthesis; hypervalent compounds; iodine; lactones; oxidation; HYPERVALENT IODINE COMPOUNDS; ASYMMETRIC OXIDATION; 4-METHYLCYCLOHEXYLIDENEMETHYLIODONIUM SALT; CATION INTERMEDIATE; VINYL CATION; REAGENTS; ION; SULFOXIDES; IODOARENES; SOLVOLYSIS;

D O I：

10.1002/anie.201003503

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

It's the hype: The asymmetric synthesis of 3-alkyl-4-oxyisochroman-1-one is achieved by oxylactonization of ortho-alk-1-enylbenzoate with a series of optically active hypervalent iodine(III) reagents prepared from lactate or valine as a chiral source (see scheme). The oxylactonization is highly regio-, diastereo-, and enantioselective. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7068 / 7071

页数：4

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