期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 47, 页码 17041-17044出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja108238a
关键词
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资金
- New Century Excellent Talents in University
- Ministry of Education, China [NCET-07-0283]
- Shanghai Committee of Science and Technology [06PJ14023]
- 111 Project [B07023]
- ERDF AWMII
- University of Birmingham
Novel planar chiral ferrocene nucleophilic catalysts (Fc-PIP) containing both central and planar chiral elements were designed and synthesized for catalytic enantioselective acyl transfer of secondary alcohols. A remarkably efficient catalyst with high selectivity factors (up to S = 1892) was identified. Comparing the combination of central and planar chirality revealed a strong requirement for the matched chiral elements, indicating that the stereogenic center of the imidazole rings should present itself on the same face as the ferrocenyl fragment; otherwise, the catalyst is completely inactive. An exclusively stacked transition state that accounts for the high selectivity of the kinetic resolution of secondary alcohols is proposed. Notably, this newly designed catalyst family is suitable for the catalytic kinetic resolution of bulky arylalkyl carbinols, producing esters with extremely high ee (>99%).
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