Accelerated and enantioselective synthesis of a library of p-stereogenic urea phosphines
| Title | Accelerated and enantioselective synthesis of a library of p-stereogenic urea phosphines |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Koshti, VS, Gote, RP, Chikkali, SH |
| Journal | European Journal Of Organic Chemistry |
| Issue | 47 |
| Pagination | 6768-6779 |
| Date Published | DEC |
| Type of Article | Article |
| ISSN | 1434-193X |
| Abstract | Chiral phosphorus ligands play a central role in majority of the asymmetric transformations. However, access to chiral phosphorus ligands is limited due to their challenging synthesis. Reported here is a highly efficient and accelerated catalytic asymmetric synthesis of P-stereogenic urea containing phosphines leading to a small library of 18 chiral phosphorus compounds. Characteristic two doublets in a P-31 NMR spectrum, spectroscopic and analytical evidences authenticated the formation of [Pd-{(S,S) Me-FerroLANE}(m-phenylurea)(I)] complex. Indeed, [Pd-{(S,S) Me-FerroLANE}(m-phenylurea)(I)] was found to catalyze the C-P coupling reaction and quantitative conversion was observed within 18 hours. Under optimized conditions, iodophenyl urea's (2a-2j) were treated with secondary phosphines (1a-1c) in presence of [Pd-{(S,S) Me-FerroLANE}(m-phenylurea)(I)] to obtain P-stereogenic urea phosphines 5a-5r. The identity of these urea derived phosphines was unambiguously ascertained using a combination of spectroscopic and analytical methods. The catalyst tolerated various functional groups and yielded corresponding urea containing phosphines with an enantiomeric excess in the range of 15-62 %. |
| DOI | 10.1002/ejoc.201801309 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.882 |
Divison category:
Polymer Science & Engineering