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Digitale Medien

Highly Selective Allylation of Alkyl Methyl Ketones in the Presence of Chiral 2-Amino Alcohol Derivatives (1998)

Tietze, Lutz F. ; Wegner, Christoph ; Wulff, Christian

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 1639-1644

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Details

ISSN: 1434-193X

Schlagwort(e): Allylation ; Allylsilanes ; Amino alcohols ; Domino reactions ; Homoallylic alcohols ; Homoallylic ketones ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The facial selective allylation of alkyl methyl ketones 1a-f in the presence of chiral 2-amino alcohol derivatives 2a-p by reaction with allylsilane 3 and a catalytic amount of TfOH to give the tertiary homoallylic ethers 8a-o and 9a-e is described. The best results were obtained with the 2-amino alcohol derivative 2p which affords a stereoselectivity of 18:1 even for the allylation of ethyl methyl ketone. The ethers 8 and 9, which contain a phenyl group at C-1 of the amino alcohol moiety, can be cleaved to give the corresponding homoallylic alcohols 5 by reduction with sodium or lithium in liquid ammonia.

Materialart: Digitale Medien

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