Stereoselective synthesis of 1,3-amino alcohols by the Pd-catalyzed cyclization of trichloroacetimidates.

The synthesis of 4-vinyl-5,6-dihydro-1,3-oxazines, precursors of 1,3-amino alcohols, using the palladium-catalyzed cyclization of trichloroacetimidates is reported. The reaction favors the formation of the 4,6-cis-isomers with up to >20:1 diastereoselectivity. Chemoselective hydrolysis of the resulting 5,6-dihydro-1,3-oxazines was also investigated.