Stéréosélectiveté de la condensation aldolique. Réaction du benzaldéhyde et d'énolates carbéniates magnésiens α-chlorés

Autor:	M. C. Roux-Schmitt, Jacqueline Seyden-Penne, G. Kyriakakou
Rok vydání:	1973
Předmět:	Inorganic Chemistry chemistry.chemical_classification chemistry Stereochemistry Group (periodic table) Organic Chemistry Materials Chemistry Physical and Theoretical Chemistry Propionates Biochemistry Medicinal chemistry Alkyl
Zdroj:	Journal of Organometallic Chemistry. 47:315-320
ISSN:	0022-328X
DOI:	10.1016/s0022-328x(00)81741-6
Popis:	Alkyl chloracetates III (R′ = H) and phenylchloracetates III (R′ = Ph) condense with PhCHO in the presence of (i-Pr) 2 NMgBr giving alkyl-2-chloro-3-hydroxy-3-phenyl propionates ( RS, RS ) (I) and ( RS, SR ) (II) in equal ratio ( 1 1 ) for III (R′ = H) and in the ratio 65 35 for III (R′ = Ph) irrespective of the group R. When the same reaction is performed with alkyl chloropropionates III (R′ = CH 3 ) the isomer ratio is dependent upon the group R. These results are interpreted by considering a planar (R′ = H or Ph) or pyramidal (R′ = CH 3 ) geometry of the intermediate enolate-carbeniate.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::78c14c1c9868cc93b6b91eec5988aff5 https://doi.org/10.1016/s0022-328x(00)81741-6 Zobrazit plný text záznamu