Visible light photocatalysis of radical anion hetero-Diels-Alder cycloadditions

被引：96

作者：

Hurtley, Anna E. ^{[1
]}

Cismesia, Megan A. ^{[1
]}

Ischay, Michael A. ^{[1
]}

Yoon, Tehshik P. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA

来源：

TETRAHEDRON | 2011年 / 67卷 / 24期

关键词：

Hetero-Diels-Alder cycloaddition; Photocatalysis; Radical anion; ENANTIOSELECTIVE TOTAL-SYNTHESIS; PHOTOREDOX CATALYSIS; INTRAMOLECULAR CYCLOBUTANATION; ALDEHYDES; REDUCTION; SEGMENT; CATION;

D O I：

10.1016/j.tet.2011.02.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have discovered a photocatalytic intramolecular hetero-Diels-Alder reaction of tethered bis(enones). This transformation involves the intermediacy of an enone radical anion and constitutes the formal coupling of an electron-deficient heterodiene with an electronically mismatched enone dienophile. The diastereoselectivity and regioselectivity of the process are high, and the dihydropyran products are amenable to a variety of synthetically useful transformations. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4442 / 4448

页数：7

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