Synthesis of enantiopure β- and γ-amino alcohols from homochiral α- and β-aminoacylsilanes as stable synthetic equivalents of α- and β-amino aldehydes

Bianca Flavia Bonini, Mauro Comes-Franchini, Mariafrancesca Fochi, Jacek Gawronski, Germana Mazzanti, Alfredo Ricci, Greta Varchi

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

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 anylation 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.

Original languageEnglish (US)
Pages (from-to)437-445
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number2
DOIs
StatePublished - Feb 1999

Keywords

  • Allylation
  • Amine alcohols
  • Amine aldehydes
  • Aminoacylsilanes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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