Diastereoselective Ru-catalyzed cross-metathesis-dihydroxylation sequence. an efficient approach toward enantiomerically enriched syn-diols |
| |
Authors: | Neisius N Matthias Plietker Bernd |
| |
Affiliation: | Institut für Organische Chemie, Universit?t Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany. |
| |
Abstract: | 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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|