Diastereoselective ru-catalyzed cross-metathesis-dihydroxylation sequence. An efficient approach toward enantiomerically enriched syn-diols
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Contributors
Abstract
(Chemical Equation Presented) Sequential catalysis has evolved as a powerful concept within the past years and allows the more efficient use of catalytically active expensive transition metals in organic synthesis. In this paper we present the stereoselective cross-metathesis-dihydroxylation of various olefins with chiral auxiliary substituted acrylamides. The chiral information (i.e., the auxiliary) introduced in the metathesis reactions allows for a stereoselective subsequent RuO4-catalyzed dihydroxylation. The sequence is concluded by an unusual kinetic resolution of the diastereomeric diols obtained in the oxidation reaction. As a consequence a variety of structurally diverse enantiomerically enriched diols are obtained. To the best of our knowledge the results summarized in this paper represent the first highly efficient diastereoselective RuO4-catalyzed oxidation.
Details
Original language | English |
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Pages (from-to) | 3218-3227 |
Number of pages | 10 |
Journal | Journal of Organic Chemistry |
Volume | 73 |
Issue number | 8 |
Publication status | Published - 18 Apr 2008 |
Peer-reviewed | Yes |
Externally published | Yes |
External IDs
ORCID | /0000-0001-8423-6173/work/161891585 |
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