Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.
Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.
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DOI：
10.1021/acs.orglett.5b01447
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发表时间：
2015-07-02
期刊：
影响因子：
5.2
通讯作者：
Stanley LM
中科院分区：
文献类型：
--
作者：
Du XW;Stanley LM
报道了一系列反应，包括Rh催化的炔烃与水杨醛的分子间氢酰化反应和分子内的氧迈克尔加成反应，用于2，3-二取代色满-4-酮的非对映选择性合成。从一系列1，2-二取代的乙苯和取代的水杨醛，通过串联的氢酰化/氧代-Michael加成反应高产率地生成2，3-二取代色满-4-酮。得到的2，3-二取代色满-4-酮很容易氟化，以高产率形成trans-3-fluoro-2，3-disubstituted-chroman-4-ones，具有良好的非对映选择性。
Tandem reactions involving Rh-catalyzed intermolecular hydroacylations of alkynes with salicylaldehydes followed by intramolecular oxo-Michael additions are described for the diastereoselective synthesis of 2,3-disubstituted chroman-4-ones. The tandem hydroacylation/oxo-Michael additions occur to form 2,3-disubstituted chroman-4-ones in high yields from a range of 1,2-disubstituted acetylenes and substituted salicylaldehyes. The resulting 2,3-disubstituted chroman-4-ones are readily fluorinated to form trans-3-fluoro-2,3-disubstituted-chroman-4-ones in high yields with excellent diastereoselectivity.