The diastereoselective preparation of syn-β-hydroxycyanohydrins by addition of cyanide to β-hydroxyketones with dimethyldicyanosilane

Autor:	Ernesto Brunet, Manohar Singh Batra
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Addition reaction Stereochemistry Cyanide Organic Chemistry Intermolecular force Reaction intermediate Biochemistry chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Aliphatic compound Alkyl Cyanohydrin
Zdroj:	Tetrahedron Letters. 34:711-714
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(00)61660-x
Popis:	The addition of cyanide with Me 2 Si(CN) 2 to β-hydroxyketones (R 1 CHOH-COR 2 , R 1 = R 2 = alkyl) took place with high diastereoselectivity ( > 95% d.e.) and reasonable overall isolated yield (60%). The syn configuration of the produced β-hydroxycyanohydrin seems compatible only with intermolecular addition of CN, through a chair-like six-membered transition state.
Databáze:	OpenAIRE
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