Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes

被引：29

作者：

Parhi, Biswajit ^{[1
]}

Gurjar, Jitendra ^{[1
]}

Pramanik, Suman ^{[1
]}

Midya, Abhisek ^{[1
]}

Ghorai, Prasanta ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 11期

关键词：

ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; KETONES; DESYMMETRIZATION; ALKOXYBORONATE; PEROXIDATION; DERIVATIVES; CYCLIZATION; EPOXIDATION; ALDEHYDES;

D O I：

10.1021/acs.joc.6b00565

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented enantioselective intramolecular oxa-Michael reaction of enols has been described. A squaramide-containing tertiary amine based bifunctional organocatalyst efficiently activates the o-homoformyl chalcones to provide the chiral isochromenes in moderate yields and good to excellent enantioselectivities. Further, late-stage functionalizations of the vinyl ether moiety of the chiral isochromene products have also been exemplified.

引用

页码：4654 / 4663

页数：10

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