Asymmetric Synthesis of β-Methylated Aliphatic Ketones via Lithiated 3-[(S)-2-(Methoxymethyl)pyrrolidino]hex-3-ene⋆

Autor:	Rainer Schmidt, Hubertus Ahlbrecht, Uwe Beyer
Rok vydání:	1998
Předmět:	chemistry.chemical_compound Chiral auxiliary chemistry Organic Chemistry Butyllithium Enantioselective synthesis Organic chemistry Ether Physical and Theoretical Chemistry Alkylation Ene reaction Enamine Prolinol
Zdroj:	European Journal of Organic Chemistry. 1998:1371-1377
ISSN:	1099-0690 1434-193X
DOI:	10.1002/(sici)1099-0690(199807)1998:7<1371::aid-ejoc1371>3.0.co;2-k
Popis:	3-Substituted aliphatic ketones 10 have been obtained in excellent optical yields by alkylation of the aminoallyllithium compound endo-8, a homoenolate equivalent of hexane-3-one, using prolinol ether (SMP) as the chiral auxiliary. The intermediate endo-8 was generated by tin–lithium exchange of the 3-stannylated enamine 7a with butyllithium. An improved hydrolysis procedure for the resulting enamines is described. Some mechanistic implications with respect to the formation as well as the alkylation of endo-8 are discussed.
Databáze:	OpenAIRE
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