Barbier-type diastereoselective allylation of alpha-amino aldehydes with an enantiopure 2-sulfinylallyl building block.
An optimized procedure for the diastereoselective allylation under aqueous Barbier conditions of a series of alpha-amino aldehydes with our new chiral building block (S(s))-3-chloro-2-(p-tolylsulfinyl)-1-propene [(S(s))-1a] to afford enantiomerically pure sulfinylamino alcohols in good yields and diastereoselectivites is reported. High levels of diastereoinduction can be achieved from alpha-amino aldehydes configurationally related to natural alpha-amino acids.
Márquez
Francesc
F
Universitat de Barcelona, Facultat de Farmàcia, Unitat de Química Farmacèutica, Unitat Associada al CSIC Avgda. Joan XXIII, s/n, 08028 Barcelona, Spain.
Montoro
Raúl
R
Llebaria
Amadeu
A
Lago
Elena
E
Molins
Elies
E
Delgado
Antonio
A