CsF in organic synthesis.: Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers
CsF in organic synthesis.: Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers
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DOI：
10.1016/s0040-4020(99)00896-0
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发表时间：
1999-12-10
期刊：
影响因子：
2.1
通讯作者：
Otera, J
中科院分区：
文献类型：
--
作者：
Kitaori, K;Furukawa, Y;Otera, J
环氧乙烷与苯酚反应路径的两种模式完全由CsF控制。诺磺酸缩水甘油酯在 C-1 位发生排他性取代，而环氧氯丙烷、缩水甘油和 1,2-环氧烷烃则发生开环（C-3 攻击）。这些反应为获得对映体纯β-受体阻滞剂提供了方便。 (C) 1999 Elsevier Science Ltd. 保留所有权利。
The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C-1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1,2-epoxyalkanes. These reactions provide convenient access to enantiopure beta-blockers. (C) 1999 Elsevier Science Ltd. All rights reserved.