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Asymmetric Synthesis of β-Methylated Aliphatic Ketones via Lithiated 3-[(S)-2-(Methoxymethyl)pyrrolidino]hex-3-ene⋆ (1998)

Ahlbrecht, Hubertus ; Schmidt, Rainer ; Beyer, Uwe

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 1371-1377

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ISSN: 1434-193X

Keywords: Homoenolate equivalents, chiral ; Alkylation ; 1-Aminoallyl anions, chiral ; β-Methyl ketones, chiral ; Asymmetric synthesis ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Type of Medium: Electronic Resource

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