Diastereoselective Paterno-Buchi reaction on furan derivatives-reaction with asymmetric ketones

被引：0

作者：

D'Auria, Maurizio ^{[1
]}

Emanuele, Lucia ^{[1
]}

Pace, Vita ^{[1
]}

Racioppi, Rocco ^{[1
]}

机构：

[1] Univ Basilicata, Dipartimento Chim, I-85100 Potenza, Italy

来源：

LETTERS IN ORGANIC CHEMISTRY | 2006年 / 3卷 / 05期

关键词：

Paterno-Buchi reaction; 2+2 cycloaddition; chiral ketone; diastereoselectivity;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photochemical reaction of 1-phenyl-2-methyl-1-butanone with furan gave propiophenone via a Norrish Type II reaction. The same behavior was observed using 1-phenyl-2-methyl-1-pentanone. In this case, the product derived from a Norrish-Yang reaction was obtained. The photochemical reaction of 2-phenylpropiophenone with furan and 2-methylfuran gave the corresponding Paterno-Buchi adducts. 2-Methylfuran gave a mixture of regioisomers. All the products of the Paterno-Buchi reaction were obtained with >98% de. The diastereoselectivity was explained by considering the relative stability of the biradical intermediates.

引用

页码：350 / 355

页数：6

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