A novel annulation reaction has been developed for the synthesis of four-membered rings utilizing 1,2-dicarbanionic organotitanium complexes. While considerable work has described the reactions of these complexes with esters to form cyclopropanols, little is known about their interactions with other electrophiles. It is reported that the reaction of these low-valent titanium intermediates with 1,2-dielectrophiles, such as α-bromoaldehydes and α-tosylnitriles, generate substituted cyclobutanols and cyclobutanones that are not readily accessible by traditional [2+2] cycloadditions.

Titanium-mediated synthesis of substituted cyclobutanes

253rd National Meeting (2017)

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