Stereoselective nucleophilic substitution of 6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-yl acetate: application to the synthesis of a NK1 receptor antagonist

Autor:	Tomiki Hashiyama, Kazutoshi Sugawara
Rok vydání:	2007
Předmět:	Stereochemistry Organic Chemistry Biochemistry chemistry.chemical_compound chemistry Nucleophile Benzyl alcohol Pyran Yield (chemistry) Drug Discovery Nucleophilic substitution Stereoselectivity Lewis acids and bases Selectivity
Zdroj:	Tetrahedron Letters. 48:3723-3726
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2007.03.104
Popis:	Reaction of chiral cis - and trans -6-( tert -butyldimethylsilyloxy)-3,6-dihydro-2 H -pyran-3-yl acetates with various nucleophiles (allyltrimethylsilane, bistrimethylsilylacetylene, benzyl alcohol, benzyl carbamate etc.) in the presence of a Lewis acid gave the corresponding 2,3-unsaturated pyran derivatives in good to excellent yield with trans selectivity. Application to the synthesis of NK 1 antagonist is also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1cf9d9b02117e2ad260441a270a5eeee https://doi.org/10.1016/j.tetlet.2007.03.104 Zobrazit plný text záznamu Full Text from ScienceDirect