Highly stereoselective aldol reaction based on titanium enolates from (S)-1-benzyloxy-2-methyl-3-pentanone

Joan G Solsona; Joaquim Nebot; Pedro Romea; Fèlix Urpí

doi:10.1021/jo050792l

Highly stereoselective aldol reaction based on titanium enolates from (S)-1-benzyloxy-2-methyl-3-pentanone

J Org Chem. 2005 Aug 5;70(16):6533-6. doi: 10.1021/jo050792l.

Authors

Joan G Solsona¹, Joaquim Nebot, Pedro Romea, Fèlix Urpí

Affiliation

¹ Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain.

PMID: 16050726
DOI: 10.1021/jo050792l

Abstract

Alternative titanium-mediated aldol procedures based on several protected beta-hydroxy ethyl ketones have been surveyed. Eventually, enolization of (S)-1-benzyloxy-2-methyl-3-pentanone (1) with (i-PrO)TiCl3/i-Pr2NEt provided a very reactive enolate that afforded the corresponding 2,4-syn-4,5-syn aldol adducts in high yields and diastereomeric ratios with a broad range of aldehydes.