Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes.
A stereoselective synthesis of 1-substituted (E)-2-aryl-but-1-en-3-ynes, including tetrasubstituted alkenes, has been developed from aryl-substituted α-allenols by treatment with the AcCl-NaOH (aqueous) system. This transformation might be explained through the elimination of acetic acid, made up of a δ-hydrogen and the acetate group in the initially formed α-allenic acetate.
Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain. alcaideb@quim.ucm.es
Benito
B
Alcaide
Pedro
P
Almendros
Teresa
T
Martínez del Campo
D000438:Alcohols / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D000480:Alkynes