Concise asymmetric synthesis of orthogonally protected syn - And anti -1,3-aminoalcohols

Abstract

Novel chiral binfunctional reagents V and ent-V undergo asymmetric aldehyde allylation followed by Ir(I)-catalyzed enantioselective allylic amidation to give orthogonally protected syn- and anti-1,3-aminoalcohols with complete control of absolute and relative stereochemistry. The Mitsunobu reaction of the initial homoallylic alcohol products followed by Ir(I)-catalyzed enantioselective allylic amidation provides orthogonally protected syn- and anti-1,3-diamine derivatives in high yields and with excellent stereoselectivities. © 2013 American Chemical Society.