Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 2, Pages 1150-1159Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b12796
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Funding
- Fundamental Research Funds for the Central Universities in China [CQDXWL-2014-Z003, 2018CDXZ0002]
- Scientific Research Foundation of China [21772018, 21822303, 21772020]
- Ministry of Science, ICT, and Future Planning in Korea [NRF-2014R1A2A1A01005794, NRF-2016R1A4A1011451]
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The development and characterization of enantioselective catalytic kinetic resolution of allylic alcohols through asymmetric isomerization with chiral BINOL derivatives-based alkoxides as bifunctional Bronsted 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 Bronsted 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 Bronsted 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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