A phosphorimidate rearrangement for the facile and selective preparation of allylic amines.
Allylic phosphorimidates, readily prepared from the combination of an allylic alcohol, an azide, and a chlorophosphite, undergo [3,3]-rearrangement under thermal conditions to provide single isomers of allylic phosphoramidates. This new rearrangement is tolerant of a range of substitution patterns on the reactants. Treatment of the products of the rearrangement with ethanethiolate followed by acid produces a protected allylic amine. This strategy thus provides an attractive and versatile procedure for the preparation of key synthetic intermediates, allylic amines.
Chen
Bin
B
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Mapp
Anna K
AK
D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013696:Temperature
D000498:Allyl Compounds; D000588:Amines; D009943:Organophosphorus Compounds