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.
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页码：350 / 355
页数：6
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