Stereoselective Synthesis of Alkylidene Phthalides
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- 作者：Andrei Dragan ; D. Heulyn Jones ; Alan R. Kennedy ; Nicholas C. O. Tomkinson
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：July 1, 2016
- 年：2016
- 卷：18
- 期：13
- 页码：3086-3089
- 全文大小：372K
- 年卷期：0
- ISSN：1523-7052
文摘
The N,O-diacylhydroxylamine derivative 4 has been prepared and its reactivity with nucleophiles investigated. On reaction with lithium enolates of cyclic or acyclic ketones, 4 is converted stereoselectively to the corresponding alkylidene phthalide. The stereochemical outcome of the transformation can be modified by changing the polarity of the reaction medium and the products isomerized under acidic conditions.