A dramatic reversal of facial selectivity in the sharpless asymmetric dihydroxylation of a sterically hindered 3-methylidene-benzofuran

A dramatic reversal of π-facial selectivity in the osmium-catalyzed asymmetric dihydroxylation (AD) of an exocyclic olefin is reported; wherein, switching from a phthalazine-linked ligand to a pyrimidine-linked ligand led to the opposite enantiomer using the same pseudoenatiomer of the cinchona alka...

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Bibliographic Details
Published inTetrahedron letters Vol. 37; no. 9; pp. 1375 - 1376
Main Author Krysan, Damian J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.02.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A dramatic reversal of π-facial selectivity in the osmium-catalyzed asymmetric dihydroxylation (AD) of an exocyclic olefin is reported; wherein, switching from a phthalazine-linked ligand to a pyrimidine-linked ligand led to the opposite enantiomer using the same pseudoenatiomer of the cinchona alkaloid. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)00057-3