Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3+2) Cycloaddition and Its Application in the Formal Synthesis of (R)-(-)-Puraquinonic Acid

被引：5
|
作者：
Oga, Miho [1 ]
Takamatsu, Yusei [1 ]
Ogura, Akihiro [1 ]
Takao, Ken-ichi [1 ]
机构：
[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 13期
关键词：
ENANTIOSELECTIVE SYNTHESIS; ALLENOATES; SKELETON;
D O I：
10.1021/acs.joc.2c00753
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly stereoselective (3 + 2) cycloaddition for the asymmetric synthesis of versatile cyclopentene compounds containing all-carbon quaternary stereocenters was developed. The phosphine-catalyzed reactions of alkynoates with alpha-alkylated electron-deficient alkenes bearing Oppolzer's camphorsultam showed high to excellent diastereoselectivities and perfect regioselectivities. The usefulness of this reaction was demonstrated in the concise formal synthesis of (R)-(-)-puraquinonic acid.
引用
收藏
页码：8788 / 8795
页数：8
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