Asymmetric Dihydroxylation of Dienes: Synthesis of Tetrols

Michel L. Belley; Bryan Hill; Hugh Mitenko; John Scheigetz; Robert Zamboni

doi:10.1055/s-1996-5323

Synlett 1996; 1996(1): 92-94
DOI: 10.1055/s-1996-5323

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Asymmetric Dihydroxylation of Dienes: Synthesis of Tetrols

Michel L. Belley^* , Bryan Hill, Hugh Mitenko, John Scheigetz, Robert Zamboni

^*Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe Claire-Dorval, Quebec, H9R 4P8, Canada, Fax (514) 695-0693

Abstract

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The asymmetric dihydroxylation of symmetrical dienes containing either terminal or trisubstituted double bonds afforded pseudo C₂ symmetric tetrols in good yields in a stereoselective manner. The major isomer could be obtained with a synthetically useful enantiomeric excess, although β-substituents were found to have unfavorable effects on the selectivity of the reaction.

asymmetric dihydroxylation - tetrol - symmetrical diene - 2-(1-(S)-methoxyethyl)benzeneboronic acid - ADMIX-β

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