Title | THE SYNTHESIS OF ANTHRAPHOS, A CONFORMATIONALLY RIGID, C-2-SYMMETRICAL DIPHOSPHINE AND THE X-RAY CRYSTAL-STRUCTURE OF [RH(COD)(ANTHRAPHOS)]BF4 |
Publication Type | Journal Article |
Year of Publication | 1994 |
Authors | Fu, TY, Liu, ZQ, Scheffer, JR, Trotter, J |
Journal | Tetrahedron Letters |
Volume | 35 |
Pagination | 7593-7596 |
Date Published | Oct |
Type of Article | Article |
ISBN Number | 0040-4039 |
Keywords | ACID, ASYMMETRIC-SYNTHESIS, COMPLEXES, HYDROGENATION, LIGANDS, NORPHOS |
Abstract | Anthraphos (trans-9,10-dihydro-9,10-ethanoanthracene-11,12-bis(diphenylphosphine) (3), a conformationally rigid, C-2-symmetric diphosphine, has been prepared in three steps, the key step being the Diets-Alder reaction between anthracene and ethyndiylbis(diphenylphosphine oxide). Resolution of anthraphos followed by formation of the [Rh(COD)(anthraphos)]BF4 complex afforded an optically active hydrogenation catalyst precursor whose crystal and molecular structure and absolute configuration were determined by single crystal X-ray diffractometry. Use of the (R,R)-(-) form of the catalyst precursor to hydrogenate (Z)-alpha-acetamidocinnamic acid gave (S)-(+)-N-acetylphenylalanine in 90% enantiomeric excess. |
URL | <Go to ISI>://A1994PL49600027 |
