化学
动力学分辨率
烯丙基重排
对映选择合成
异构化
双功能
催化作用
反应性(心理学)
布朗斯特德-洛瑞酸碱理论
手性(物理)
醇盐
对映体
组合化学
有机化学
物理
医学
病理
量子力学
手征对称破缺
替代医学
Nambu–Jona Lasinio模型
夸克
作者
Yidong Liu,Song Liu,Dongmei Li,Nan Zhang,Lei Peng,Jun Ao,Choong Eui Song,Yu Lan,Hailong Yan
摘要
The development and characterization of enantioselective catalytic kinetic resolution of allylic alcohols through asymmetric isomerization with chiral BINOL derivatives-based alkoxides as bifunctional Brønsted base catalysts were described in the study. A number of chiral BINOL derivatives-based alkoxides were synthesized, and their structure–enantioselectivity correlation study in asymmetric isomerization identified a promising chiral Brønsted base catalyst, which afforded various chiral secondary allylic alcohols (ee up to 99%, S factor up to >200). In the mechanistic study, alkoxide species were identified as active species and the phenol group of BINOL largely affected the high reactivity and enantioselectivity via hydrogen bonding between the chiral Brønsted base catalyst and substrates. The strategy is the first successful synthesis strategy of various chiral secondary allylic alcohols through enantioselective transition-metal-free base-catalyzed isomerization. The applicability of the strategy had been demonstrated by the synthesis of the bioactive natural product (+)-veraguensin.
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