Sequenced reactions with Samarium(II) iodide.: Sequential intramolecular Barbier cyclization/Grob fragmentation for the synthesis of medium-sized carbocycles

被引：61

作者：

Molander, GA ^{[1
]}

Le Huérou, Y ^{[1
]}

Brown, GA ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 13期

关键词：

D O I：

10.1021/jo001513r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Samarium(II) iodide was used to access eight-, nine-, and ten membered carbocycles via a domino reaction composed of a cyclization/fragmentation process. 2-(Iodoalkyl)-, 2-(iodomethyl)allyl-, and 2-(2-iodomethyl)benzyl-2-methyl-3-(methanesulfonyloxy)cycloalkanones were subjected to Barbier-type reductive coupling conditions. Intermediate cycloalkanedione derivatives were also treated under similar conditions, providing bicyclic hydroxy ketones with complete diastereoselectivity and high yields. This method represents a general and efficient approach to a variety of highly functionalized, stereodefined carbocycles.

引用

页码：4511 / 4516

页数：6

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