One-pot highly enantio- and diastereoselective synthesis of anti,anti vinylic 3-amino-1,2 diols via proline catalyzed sequential alpha-amination/benzoyloxyallylation of aldehydes
| Title | One-pot highly enantio- and diastereoselective synthesis of anti,anti vinylic 3-amino-1,2 diols via proline catalyzed sequential alpha-amination/benzoyloxyallylation of aldehydes |
| Publication Type | Journal Article |
| Year of Publication | 2015 |
| Authors | Ahuja, BBhushan, Sudalai, A |
| Journal | RSC Advances |
| Volume | 5 |
| Issue | 28 |
| Pagination | 21803-21805 |
| Date Published | FEB |
| ISSN | 2046-2069 |
| Abstract | The first direct asymmetric synthesis of anti, anti vinylic 3-amino-1,2-diols from aldehydes is described via a one-pot sequential L-proline catalyzed alpha-amination/benzoyloxyallylation protocol. The reaction proceeds with exceptionally high diastereoselectivity (>99%) as can be explained based on the Felkin-Ahn transition state model. Its effectiveness is proven unambiguously by demonstrating a short asymmetric synthesis of D-ribo-phytosphingosine tetraacetate (93% ee). |
| DOI | 10.1039/c5ra02830b |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.289 |
Divison category:
Chemical Engineering & Process Development