Michael reactions of titanium enolates of glycolic acid derivatives with the Weinreb and morpholine amides of acrylic acid.
The conjugate additions of titanium enolates of glycolate-derived chiral oxazolidin-2-ones to various Michael acceptors have been evaluated as an entry to enantiopure 1,2,5-trioxygenated and related synthons. alpha,beta-unsaturated Weinreb and morpholine amides do react under suitable conditions and their adducts can be converted to diverse C1-C5 chiral fragments.
Olivella
Anna
A
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain.
Rodríguez-Escrich
Carles
C
Urpí
Fèlix
F
Vilarrasa
Jaume
J
D000179:Acrylates / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D006016:Glycolates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009025:Morpholines / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D014025:Titanium / Q000737:chemistry*
D000179:Acrylates; D000577:Amides; D006016:Glycolates; D009025:Morpholines; C031149:glycolic acid; D014025:Titanium; C036658:acrylic acid