Ni-catalyzed highly enantioselective synthesis of sulfur protected P-stereogenic supramolecular phosphine
| Title | Ni-catalyzed highly enantioselective synthesis of sulfur protected P-stereogenic supramolecular phosphine |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Koshti(S), VS, Chandanshive, AC, Mote, NR, Chikkali, SH |
| Journal | Journal of Chemical Sciences |
| Volume | 133 |
| Issue | 4 |
| Pagination | 119 |
| Date Published | DEC |
| Type of Article | Article |
| ISSN | 0974-3626 |
| Keywords | Asymmetric synthesis, Nickel catalyst, P-C coupling, P-Stereogenic phosphine, supramolecular ligands |
| Abstract | As phosphines readily invert, the synthesis of P-chiral phosphines is a challenging task and has been rarely investigated. We report the synthesis of a nickel complex [Ni-((S,S)Me-FerroLANE)(phenyl)(I)] (Ni-Cat.1) and its performance in a P-C coupling reaction to generate P-chiral phosphine. The Ni-Cat.1 was synthesized by mixing ligand (S,S) Me-FerroLANE with the metal precursor [(diphenylphosphanyl)nickel(phenyl)(I)] in good yield. Ni-Cat.1 was characterized using different spectroscopic and analytical techniques. Treatment of racemic methyl(phenyl)phosphine (1) with 1-(3-iodophenyl)urea (2) produced the corresponding P-chiral supramolecular phosphine (3). Optimization of reaction parameters produced sulfur protected phosphine N-(3-(methyl(phenyl)phosphorothioyl)phenyl)formamide (3') with excellent enantiomeric excess (99% ee) and moderate conversion (51%). |
| DOI | 10.1007/s12039-021-01978-3 |
| Type of Journal (Indian or Foreign) | Indian |
| Impact Factor (IF) | 1.573 |
Divison category:
Polymer Science & Engineering