Attempted resolution of free (±)-chlorophenylisopropylphosphine

Autor:	Anthony C. Willis, S. Bruce Wild, Michael Pabel
Rok vydání:	1995
Předmět:	Stereochemistry Organic Chemistry Diastereomer Absolute configuration chemistry.chemical_element Medicinal chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Yield (chemistry) Stereoselectivity Methanol Physical and Theoretical Chemistry Triethylamine Phosphine Palladium
Zdroj:	Tetrahedron: Asymmetry. 6:2369-2374
ISSN:	0957-4166
DOI:	10.1016/0957-4166(95)00314-f
Popis:	(±)-Chlorophenylisopropylphosphine has been resolved in a palladium(II) complex containing the phosphine and ortho-metalated ( R )-1-[1-(dimethylamino)ethyl]naphthalene; the configurationally homogeneous ( R , R p ) diastereomer of the complex crystallises from the reaction mixture by typical second-order asymmetric transformation in overall 82% yield. The absolute configuration of the complex was determined by X-ray crystallography. The pure ( R , R p ) diastereomer of the complex reacts quantitatively with methanol in the presence of triethylamine to give the corresponding methoxyphosphine complex with complete stereoselectivity and inversion at phosphorus. All attempts at liberating optically active chlorophosphine from the palladium complex were unsuccessful.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::682a33c29be9f731414b5f8c88ca1781 https://doi.org/10.1016/0957-4166(95)00314-f Zobrazit plný text záznamu Full Text from ScienceDirect