Diastereoselective Synthesis of Vicinal Tertiary Diols

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• 作者：Brad M. Loertscher ; Phil R. Young ; Patrick R. Evans ; Steven L. Castle
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：April 19, 2013
• 年：2013
• 卷：15
• 期：8
• 页码：1930-1933
• 全文大小：256K
• 年卷期：v.15,no.8(April 19, 2013)
• ISSN：1523-7052

文摘

A strategy for the synthesis of differentiated vicinal tertiary diols is described. The key step is a high-yielding, diastereoselective LaCl₃路2LiCl-mediated addition of a Grignard or organolithium reagent to ketone 2a. The reaction is believed to proceed via a 1,3-chelated intermediate. One of the adducts has been transformed into a functionalized cyclopentenone resembling the core structure of pactamycin.