Asymmetric Synthesis of Dihydrocoumarins through Chiral Phosphoric Acid-Catalyzed Cycloannulation of para-Quinone Methides and Azlactones

被引：113

作者：

Zhang, Zhi-Pei ^{[1
]}

Xie, Kai-Xue ^{[1
]}

Yang, Chen ^{[1
]}

Li, Man ^{[1
]}

Li, Xin ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, State Key Lab Elementoorgan Chem, Coll Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 01期

关键词：

DIELS-ALDER REACTION; 1,6-CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; STEREOGENIC CENTERS; QUATERNARY CENTERS; ARYLBORONIC ACIDS; EXPEDIENT ACCESS; SULFONIUM SALTS; DERIVATIVES; KETONES;

D O I：

10.1021/acs.joc.7b02750

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral phosphoric acid-catalyzed approach constructing dihydrocoumarin motifs by the addition of azlactones to para-quinone methides (p-QMs) was developed. The reaction proceeded smoothly with a wide range of p-QMs and azlactones to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the stereoselectivity.

引用

页码：364 / 373

页数：10

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