Synthesis of Bicyclo[2.2.2]octanes with a Quaternary Bridgehead Carbon by Diphenylprolinol Silyl Ether-mediated Domino Reaction
Synthesis of Bicyclo[2.2.2]octanes with a Quaternary Bridgehead Carbon by Diphenylprolinol Silyl Ether-mediated Domino Reaction
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二苯脯氨醇甲硅烷基醚介导的多米诺反应合成具有季桥头碳的双环[2.2.2]辛烷
DOI：
10.1002/ajoc.202100573
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Yujiro Hayashi
中科院分区：
文献类型：
--
作者：
Nariyoshi Umekubo;Tohru Taniguchi;Kenji Monde;Yujiro Hayashi
采用二苯基脯氨酸硅基醚介导的α，β -不饱和醛和环己烯- 2 -烯- 1 -酮的多米诺Michael/Michael反应，在3 -位上有一个吸电子基团，合成了具有良好非对映选择性的具有近光学纯度的双环[2.2.2]辛烷衍生物。碳腈、烷氧羰基和磺酰基取代基成功地在环己烯- 2 -烯- 1 -酮的3 -位上作为合适的吸电子基团。
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 α,β‐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.