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A conceptually novel, high yielding, mono- or bis- homologation realized with lithium halocarbenoids enables the one-step, fully chemocontrolled assembling of a new class of quaternary trifluoromethyl-aziridines. Trifluoroacetimidoyl chlorides (TFAIC) act as convenient electrophilic platforms enabling the addition of one or two homologating elements by simply controlling the stoichiometry of the process. Mechanistic studies highlighted that the homologation event - carried out with two different carbenoids (LiCH2Cl and LiCH2F) - conducts to fluoromethyl-analogues, in which the first nucleophile is employed for constructing the cycle and, the second for decorating the resulting molecular architecture.
PMID: 30548145 [PubMed - as supplied by publisher]