Synthesis of Bicyclo[2.2.2]octanes with a Quaternary Bridgehead Carbon by Diphenylprolinol Silyl Ether-mediated Domino Reaction

被引：1
|
作者：
Umekubo, Nariyoshi [1 ]
Taniguchi, Tohru [2 ]
Monde, Kenji [2 ]
Hayashi, Yujiro [1 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
[2] Hokkaido Univ, Fac Adv Life Sci, Frontier Res Ctr Adv Mat & Life Sci, Sapporo, Hokkaido 0010021, Japan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 10卷 / 12期
关键词：
asymmetric synthesis; domino reaction; Michael reaction; quaternary carbon; organocatalyst; ORGANOCATALYTIC CASCADE REACTIONS; ASYMMETRIC MICHAEL REACTION; ENANTIOSELECTIVE SYNTHESIS; CYCLOADDITIONS; STEREOCENTERS; BIOSYNTHESIS; ALKALOIDS; ALDEHYDES; ENALS; BOND;
D O I：
10.1002/ajoc.202100573
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bicyclo[2.2.2]octane derivatives possessing a quaternary bridgehead carbon were synthesized with excellent diastereoselectivity in nearly optically pure form by diphenylprolinol silyl ether mediated domino Michael/Michael reaction of alpha,beta-unsaturated aldehyde and cyclohex-2-en-1-one bearing an electron-withdrawing group at the 3-position. Carbonitrile, alkoxycarbonyl, and sulfonyl substituents were successfully employed as a suitable electron-withdrawing group at the 3-position of cyclohex-2-en-1-one.
引用
收藏
页码：3261 / 3265
页数：5
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