Telescoped, Divergent, Chemoselective C1 and C1-C1 Homologation of Imine Surrogates: Access to Quaternary Chloro- and Halomethyl Trifluoromethyl Aziridines

Abstract

A conceptually novel, high-yielding, mono- or bis homologation was realized with lithium halocarbenoids and enables the one-step, fully chemocontrolled assembly of a new class of quaternary trifluoromethyl aziridines. Trifluoroaceti midoyl chlorides (TFAICs) act as convenient electrophilic platforms, enabling the addition of either one or two homo logating elements by simply controlling the stoichiometry of the process. Mechanistic studies highlighted that the homolo gation event, carried out with two different carbenoids (LiCH2Cl and LiCH2F), leads to fluoromethyl analogues in which the first nucleophile is employed for constructing the cycle and the second for decorating the resulting molecular architecture.