Regiospecific conversion of oxiranes, oxetanes, and lactones into difunctional nitrogen compounds via aminosilanes and aminostannanes

The insertion reactions of Me3SiNEt2 (I) and Me3SnNEt2 (II) into oxirane, oxetane, and lactone rings were examd. The Et2AlCl- or AlCl3-catalyzed reactions of monoalkyloxiranes and monoalkyl- or aryloxetanes gave regioisomerically pure β- and γ-amino alcs., resp.; with polysubstituted oxiranes a low of regioselectivity was generally obsd. Ring-opening reactions of the lactone rings with I gave β-amino acids or ω-hydroxy amides, depending on the ring size. With II, spontaneous ring cleavage of alkyloxiranes and of β-propiolactone occurred with reverse regioselectivity, whereas oxetanes and γ- and δ-lactones were opened with the same regioselectivity as that obtained with I for these systems.