Facile enantioselective synthesis of (S)-N-(5-chlorothiophene-2-sulfonyl)-beta,beta-diethylalaninol via proline-catalyzed asymmetric alpha-aminooxylation and alpha-amination of aldehyde
| Title | Facile enantioselective synthesis of (S)-N-(5-chlorothiophene-2-sulfonyl)-beta,beta-diethylalaninol via proline-catalyzed asymmetric alpha-aminooxylation and alpha-amination of aldehyde |
| Publication Type | Journal Article |
| Year of Publication | 2010 |
| Authors | Rawat, V, Chouthaiwale, PV, Chavan, VB, Suryavanshi, G, Sudalai, A |
| Journal | Tetrahedron Letters |
| Volume | 51 |
| Issue | 50 |
| Pagination | 6565-6567 |
| Date Published | DEC |
| ISSN | 0040-4039 |
| Keywords | alpha-Amination, alpha-Aminooxylation, Alzheimer's disease, Amino alcohol, Proline |
| Abstract | A high-yielding enantioselective synthesis of the bioactive (S)-N-(5-chlorothiophene-2-sulfonyl)beta,beta-diethylalaninol (1), a Notch-1-sparing gamma-secretase inhibitor metabolite (with EC50 = 28 nM) effective in reduction of All production in vivo, has been realized starting from readily available 3-pentanone. The key steps of the synthesis are proline-catalyzed alpha-aminooxylation and alpha-amination of aldehyde: the latter contributing an overall yield of 45.2% and 98% ee. (C) 2010 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2010.10.029 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.618 |
Divison category:
Chemical Engineering & Process Development