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A Novel One-Pot Stereoselective Synthesis of N-Protected α-Amino Acids from Morita-Baylis-Hillman Acetates
| Content Provider | Scilit |
|---|---|
| Author | Yadav, Lal Dhar Singh Rai, Vijai Kumar Singh, Santosh |
| Copyright Year | 2009 |
| Description | The first example of an operationally simple direct regio- and diastereoselective introduction of N-protected α-amino acids into Morita-Baylis-Hillman (MBH) acetates is reported. The DABCO-catalyzed reaction of MBH acetates with 2-phenyl-1,3-oxazol-5-one affords N-protected α-amino acids regioselectively in excellent yield (81-93%) with high diastereoselectivity (>92%) at ambient temperature. The synthetic protocol involves $S_{N}2′-S_{N}$2′ reaction and water-driven ring-opening cascades in a one-pot procedure, which are salient features of the present investigation. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0029-1217164.pdf |
| Ending Page | 1428 |
| Page Count | 6 |
| Starting Page | 1423 |
| ISSN | 09365214 |
| e-ISSN | 14372096 |
| DOI | 10.1055/s-0029-1217164 |
| Journal | Synlett |
| Issue Number | 09 |
| Volume Number | 2009 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2009-05-13 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synlett Organic Chemistry Morita-baylis-hillman Reaction Sn2 Reaction Α-amino Acids Regio- and Diastereoselective One-pot Synthesis |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry |
