High chelation control of three contiguous stereogenic centers in the Reformatsky reactions of indium enolates with α-hydroxy ketones:: Unexpected stereochemistry of lactone formation

被引：37

作者：

Babu, Srinivasarao Arulananda ^{[1
]}

Yasuda, Makoto ^{[1
]}

Okabe, Yuji ^{[1
]}

Shibata, Ikuya ^{[1
]}

Baba, Akio ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 14期

关键词：

D O I：

10.1021/ol060943m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A boat-type of chelated bicyclic transition state involving highly diastereoselective construction of three contiguous stereogenic centers in the Reformatsky reaction of indium enolates with alpha-alkoxy/hydroxy ketones is proposed. alpha-Hydroxy ketones with indium enolates furnished highly diastereoselective lactones, while alpha-alkoxy ketones gave acyclic esters in moderate selectivities. X-ray structure analyses of key products unequivocally revealed the unexpected stereochemistry of products and the reaction pathway.

引用

页码：3029 / 3032

页数：4

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