Regiospecific Conversion of Oxiranes, Oxetanes, and Lactones into Difunctional Nitrogen Compounds via Aminosilanes and Aminostannanes.

The insertion reactions of diethylaminotrimethylsilane (TMSDEA) and diethylaminotrimethylstannane (TMSnDEA) into oxirane, oxetane, and lactone rings are reported. Regioisomerically pure beta and gamma-amino alcohols were obtained, with AICI3 or Et2AICI catalysis, from monoalkyloxiranes and monoalkyland aryl-oxetanes respectively, whereas, in the majority of cases, reactions involving polysubstituted oxiranes resulted in a loss of regioselectivity. Ring-opening reactions of the lactone rings with TMSDEA led, on the other hand, to beta-amino acids or to omega- hydroxyamides depending upon the ring size. With TMSnDEA, spontaneous ring cleavage of the alkyloxiranes and of beta-propioJactone occurred with reversed regioselectivity, while the oxetanes and gamma- and delta-Iactones were opened with the same regiochemistry as that found with TMSDEA for the same ring systems.