期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 14, 页码 6286-6295出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja2118392
关键词
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资金
- National Institute of General Medical Sciences, National Institutes of Health [GM36700]
- National Science Foundation [OCI-1053575]
Quantum mechanical calculations reveal the origin of diastereo- and enantioselectivities of aldol reactions between aldehydes catalyzed by histidine, and differences between related reactions catalyzed by proline. A stereochemical model that explains both the sense and the high levels of the experimentally observed stereoselectivity is proposed. The computations suggest that both the imidazolium and the carboxylic acid functionalities of histidine are viable hydrogen-bond donors that can stabilize the cyclic aldolization transition state. The stereoselectivity is proposed to arise from minimization of gauche interactions around the forming C-C bond.
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