Expeditious Assembly of a 2-Amino-4H-chromene Skeleton by Using an Enantioselective Mannich Intramolecular Ring Cyclization-Tautomerization Cascade Sequence

被引：115

作者：

Ren, Qiao ^{[1
]}

Siau, Woon-Yew ^{[1
]}

Du, Zhiyun ^{[2
]}

Zhang, Kun ^{[2
]}

Wang, Jian ^{[1
]}

机构：

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

[2] Guang Dong Univ Technol, Fac Engn & Light Ind, Guangzhou 510006, Guangdong, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 28期

关键词：

asymmetric catalysis; cascade reaction; chromene; indane; organocatalysis; thiourea; THROUGHPUT SCREENING ASSAY; ALPHA-AMIDO SULFONES; AZA-HENRY REACTION; IN-SITU; N-BOC; APOPTOSIS INDUCERS; PRIVILEGED STRUCTURES; MICHAEL REACTION; DISCOVERY; DERIVATIVES;

D O I：

10.1002/chem.201100927

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Easy to assemble! An enantioselective cascade Mannich intramolecular ring cyclization-tautomerization reaction of malononitrile with 2-hydroxyl N-protected α-amido sulfone is described (see scheme), which provides a new route to the synthesis of the privileged scaffold 2-amino-4H-chromene in high yields (up to 94 %) and with good to high enantiomeric excesses (74-89 % ee). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7781 / 7785

页数：5

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