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

页码：8788 / 8795

页数：8

共 22 条

[21] Copper-Catalyzed Asymmetric Propargylic [3+2] Cycloaddition: Synthesis of Enantioenriched Dihydrofuro[3,2-c]coumarins and its Quinolinone and Thiocoumarin Analogues
Rohilla, Shweta
Shah, Sadhna
Singh, Vinod K. K.
ORGANIC LETTERS, 2023, 25 (20) : 3733 - 3738
[22] Asymmetric Synthesis of All Four Isomers of an Unusual Heterocycle-Containing Amino Acid: 2-Amino-3-furan-2-yl-pentanoic Acid
Nie Lei
Yang Rui
Zhang Conghai
Yin Haichuan
Yan Shengjiao
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CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (02) : 460 - 465

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