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  • Acylsilanes  (1)
  • Amino alcohols  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of Enantiopure β- and γ-Amino Alcohols from Homochiral α- and β-Aminoacylsilanes as Stable Synthetic Equivalents of α- and β-Amino Aldehydes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 437-445 
    Details
    ISSN: 1434-193X
    Keywords: Aminoacylsilanes ; Amino aldehydes ; Amino alcohols ; Allylation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A practical route is described for the synthesis of enantiopure β- and γ-amino alcohols with two stereocenters, starting from homochiral α- (1 and 5) and β- (13 and 16) -aminoacylsilanes, and involving stereoselective addition of allylmetal compounds and subsequent stereospecific protiodesilylation of the adducts. The degree of diastereoselectivity achieved in the nucleophilic addition step depends on both the nitrogen-protecting group and the reagents used. Diastereomeric excess (de) values equal to or higher than 98% were obtained in the TiCl4-promoted allylation of the N-Pht-aminoacylsilanes 1 and 13 and of the N-Ts-aminoacylsilane 5 with allyltrimethylsilane. Lower de values were obtained in the Sc(OTf)3-catalyzed allylation of 5 with tetraallyltin and in the additions of both allyltrimethylsilane and tetraallyltin to the N-Ts-β-aminoacylsilane 16. Protiodesilylation of the adducts, leading to the β- and γ-amino alcohols, was accomplished with TBAF, except in the case of the adducts obtained from 5. For these, a preliminary removal of the tosyl group was necessary, which was accomplished with simultaneous desilylation by treatment with Na in liquid ammonia.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98342_s.pdf or from the author.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Phosphanalkylene, 54. Synthese und Eigenschaften von Bis(trimethylsilyl)keton (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 415-418 
    Details
    ISSN: 0947-3440
    Keywords: Phosphonium ylides ; Oxidation ; Acylsilanes ; Ketone, bis(trimethylsilyl) ; Ionisation energy ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Phosphane Alkylenes, 54, - Synthesis and Properties of Bis(trimethylsilyl) KetoneThe synthesis of the bis(trimethylsilyl) ketone (1b) by oxydation of [bis(trimethylsilyl)methylene]triphenylphosphorane (3) is described. The IR, UV, NMR, and PE spectra as well as the cyclovoltagram of this compound are discussed and compared with those of di-tert-butyl ketone (13) and tert-butyl-trimethylsilyl ketone (10).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950250
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