ChemInform Abstract: Asymmetric Hydrogenation Reactions Mediated by a New Class of Bicyclic Bisphosphinites

Autor:	Stanley M. Roberts, Ulrich Berens, Manuela Ohff, Cyril B. Dousson, Mark J. Burk, Nadine Derrien
Rok vydání:	2010
Předmět:	chemistry.chemical_compound chemistry Bicyclic molecule Yield (chemistry) Asymmetric hydrogenation Diol chemistry.chemical_element Alcohol General Medicine Medicinal chemistry Catalysis Rhodium
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200004034
Popis:	The bicyclic alcohol (−)- 4 was prepared from (−)-bicyclo[3.2.0]hept-2-en-6-one (−)- 1 in 50% yield. The diol (−)- 4 was coupled to selected chlorophosphines 6 – 12 to produce a series of bisphosphinites 13 – 19 in 89–95% yield. From these bisphosphinites were prepared the rhodium complexes 20 – 26 which were characterised by 31 P NMR and used in situ for the asymmetric hydrogenation of α-enamides 27 – 29 . Complexes 21 , 23 – 25 proved to be the superior catalysts for the production of ( R )- N -acetylphenylalanine (91, 84, 90 and 87.5% ee) from 27 and ( S )- N -acetylalanine methyl ester (70, 72, 68 and 71% ee) from 28 .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::022e1017fa315f5c9751edea1b213521 https://doi.org/10.1002/chin.200004034 Zobrazit plný text záznamu Plný text