Reactions of Norbornen-7-one with Organolithium Reagents

Autor:	F. R. S. Clark, J. Warkentin
Rok vydání:	1971
Předmět:	Chemistry Stereochemistry Reagent Organic Chemistry General Chemistry Solvent effects Selectivity Medicinal chemistry Catalysis
Zdroj:	Canadian Journal of Chemistry. 49:2223-2228
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v71-362
Popis:	Alkyllithium reagents (RLi: R = methyl, n-butyl, t-butyl) add to norbornen-7-one either without stereochemical preference (R = n-butyl) or with syn attack favored. This addition selectivity is qualitatively the same as that shown by corresponding alkylmagnesium reagents but competition from reduction is much less important in the case of alkyllithium reagents.Phenyllithium and vinyllithium add preferentially from the anti face, although the corresponding Grignard reagents add selectively from the syn face. Possible causes of the stereoselectivities are considered. Solvent effects on the stereochemistry of addition are small.
Databáze:	OpenAIRE
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