Synthesis of bicyclic cyclopropylamines by intramolecular cyclopropanation of N-allylamino acid dimethylamides

Article abstract of DOI:10.1021/ol9910520

(formula presented) Cyclopropylamines and substituted cyclopropylamines are important building blocks or substituents in a variety of biologically active compounds. Here, we report the facile syntheses of cyclopropylamines by Ti(II)-mediated intramolecular coupling of a terminal olefinic moiety and the N,N-dimethylcarboxamide moiety of amino acid derivatives. The products have novel and strained bicyclic structures. The yields were good (78-83%) for all three substrates with diastereomeric ratios of about 3:1.