Asymmetric syntheses of 3-substituted-cyclohexanone derivatives by stereoselective conjugate addition to chiral 2-substituted-2-cyclohexen-1-ones

Autor:	Roger E. Harrington, Arthur G. Schultz
Rok vydání:	1991
Předmět:	inorganic chemicals Addition reaction Chiral auxiliary Chemistry Enantioselective synthesis Cyclohexanone General Chemistry Oxime Biochemistry Medicinal chemistry Catalysis Pyrrolidine chemistry.chemical_compound Colloid and Surface Chemistry Enone Conjugate
Zdroj:	Journal of the American Chemical Society. 113:4926-4931
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00013a031
Popis:	Chiral 2-substituted-2-cyclohexen-1-one 2a is prepared. Conjugate additions of organometallic reagents to 2a occur with good to excellent diastereoselectivities. Enone 2b, which contains an additional potentially coordinating oxygen atom on the side chain of the chiral auxiliary, gave about the same stereoselectivity as 2a. The chiral auxiliary (S)-(+)-2-(methoxymethyl)pyrrolidine can be removed from the product of conjugate addition by treatment with hydroxylamine hydrochloride and sodium acetate in 95% ethanol at 60°C to give an oxime of a 3-substituted cyclohexanone
Databáze:	OpenAIRE
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