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)|
|Number of pages||5|
|Journal||Journal of Organometallic Chemistry|
|State||Published - Apr 1 2001|
Bibliographical noteFunding Information:
Financial assistance from the Purdue Borane Research Fund is gratefully acknowledged.
- Asymmetric synthesis