Enantioselective Epoxidation of Nonconjugated cis-Olefins by Chiral Dioxirane

A variety of nonconjugated cis-olefins has been enantioselectively epoxidized with chiral ketones 2, and up to 92% ee has been obtained. The two prochiral faces of an olefin are likely stereodifferentiated by the relative hydrophobicity of the olefin substituents and/or allylic oxygen functionality.

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Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2009-11, Vol.11 (22), p.5150-5153
Hauptverfasser:	Burke, Christopher P, Shi, Yian
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes - chemistry Epoxy Compounds - chemical synthesis Epoxy Compounds - chemistry Hydrophobic and Hydrophilic Interactions Ketones - chemistry Molecular Structure Stereoisomerism
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Beschreibung
Zusammenfassung:	A variety of nonconjugated cis-olefins has been enantioselectively epoxidized with chiral ketones 2, and up to 92% ee has been obtained. The two prochiral faces of an olefin are likely stereodifferentiated by the relative hydrophobicity of the olefin substituents and/or allylic oxygen functionality.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol901724v