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FUNCTIONALIZATION OF FOUR-MEMBERED CYCLIC SULFOXIMINES BY A CONVENIENT LITHIATION/TRAPPING SEQUENCE

Arianna Tota, Flavio Fanelli, Aurelia Falcicchio, Renzo Luisi, Leonardo DEGENNARO
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Abstract


The functionalization of four-membered cyclic sulfoximine, based on a lithiation/electrophile trapping sequence, led to unprecedented C(2)-substituted N-Boc-1-imino-1-imino-1λ6-thietane 1-oxide in moderate to good yields. Interestingly, the reaction proceeded with high stereocontrol showing a preferential bias for an introduction of the electrophile syn to the oxygen on the sulfur. Starting from thietan-1-one, by a combination of lithiation/electrophile trapping followed by N-transfer, it is possible to obtain the stereoisomer bearing the electrophile syn to the nitrogen on the sulfur. Thus, all stereoisomers can be accessible for medicinal chemistry studies.


Keywords


cyclic sulfoximines; four-membered heterocycles; lithiation; stereoselectivity; N-transfer

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