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

• Published in: Tetrahedron letters Vol. 37; no. 9; pp. 1375 - 1376
• Main Author: Krysan, Damian J.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 26.02.1996; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology

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...