Abstract
Acrylic esters of homoallylic alcohols prepared in 92-96% ee via the asymmetric allylboration of appropriate aldehydes with B-allyldiisopinocampheylborane, upon ring-closing metathesis in the presence of 10mol% of Grabbs' catalyst provided the corresponding 6-substituted dihydropyran-2-ones. These were diastereoselectively epoxidized and regioselectively reduced to furnish optically pure analogs of statin drugs. This procedure allows for the development of a combinatorial library of analogs of these drugs.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 239-243 |
| Number of pages | 5 |
| Journal | Journal of Organometallic Chemistry |
| Volume | 624 |
| Issue number | 1-2 |
| DOIs | |
| State | Published - Apr 1 2001 |
Bibliographical note
Funding Information:Financial assistance from the Purdue Borane Research Fund is gratefully acknowledged.
Keywords
- Allylboration
- Asymmetric synthesis
- Epoxidation
- Metathesis
- Reduction
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