Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones
| Title | Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones |
| Publication Type | Journal Article |
| Year of Publication | 2007 |
| Authors | Tiwari, DKumar, Shaikh, AY, Pavase, LS, Gumaste, VK, Deshmukh, ARakeeb A |
| Journal | Tetrahedron |
| Volume | 63 |
| Issue | 11 |
| Pagination | 2524-2534 |
| Date Published | MAR |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | 3-diones, azetidin-2, azetidin-2-ones, beta-lactam, Grignard reaction |
| Abstract | Azetidin-2,3-diones have been used as synthons for the synthesis of C-3 alkylidene/alkylazetidin-2-ones. Some of the 3-alkylazetidin-2-ones are well known for their cholesterol absorption inhibitor activity. A regio and stereoselective Grignard reaction on a keto group followed by dehydration using PPh3/CCl4 reagent is a key step in this synthesis. Hydrogenation of the 3-alkylideneazetidin-2-ones provided stereoselectively cis-3-alkylazetidin-2-ones in very good yields. (c) 2006 Published by Elsevier Ltd. |
| DOI | 10.1016/j.tet.2006.12.010 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.645 |
Divison category:
Organic Chemistry