Enantioselective synthesis of cyclopropane aminoalcohols containing quaternary stereogenic centers |
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Institution: | 1. Minghang Hospital & Department of Microbiological and Biochemical Pharmacy at School of Pharmacy, Fudan University, Shanghai 201199, China;2. Department of Medicinal Chemistry at School of Pharmacy, Fudan University, Shanghai 201203, China |
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Abstract: | Some title compounds have been synthesized in enantiomerically pure form starting from d- or l-glyceraldehyde as chiral precursors. A new synthesis of (+)-(Z)-methanohomoserine, one of the key intermediates employed, is also described. The target molecules are densely functionalized. Thus, in addition to one or two hydroxyl groups on a side-chain, an amino group is attached to a quaternary carbon of the cyclopropane ring, and the fourth substituent of such a stereogenic center contains a halogen atom, an alkyl group, or an alcohol, thioether or ester function. Some of these compounds are useful precursors in the synthesis of new cyclopropane nucleosides. |
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