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THE SYNTHESIS OF ANTHRAPHOS, A CONFORMATIONALLY RIGID, C-2-SYMMETRICAL DIPHOSPHINE AND THE X-RAY CRYSTAL-STRUCTURE OF [RH(COD)(ANTHRAPHOS)]BF4

TitleTHE SYNTHESIS OF ANTHRAPHOS, A CONFORMATIONALLY RIGID, C-2-SYMMETRICAL DIPHOSPHINE AND THE X-RAY CRYSTAL-STRUCTURE OF [RH(COD)(ANTHRAPHOS)]BF4
Publication TypeJournal Article
Year of Publication1994
AuthorsFu, TY, Liu, ZQ, Scheffer, JR, Trotter, J
JournalTetrahedron Letters
Volume35
Pagination7593-7596
Date PublishedOct
Type of ArticleArticle
ISBN Number0040-4039
KeywordsACID, 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