Enantioselective synthesis of cyclopropane aminoalcohols containing quaternary stereogenic centers

Joan Rifé, Rosa M. Ortuño

Research output: Contribution to journalArticleResearchpeer-review

25 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)4245-4260
JournalTetrahedron Asymmetry
Volume10
Issue number21
DOIs
Publication statusPublished - 29 Oct 1999

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