Cyclic -sulfonyl aldimines are well-known aza-[2]-synthons for various [2 + ] annulation reactions. Herein we describe a novel base mediated [2 + 1] annulation and a regioselective aziridine ring-opening reaction cascade, which provides an efficient and distinct synthetic strategy from readily available cyclic -sulfonyl aldimines and -carbonyl sulfonium salts leading to -amino ketone derivatives through the corresponding fused tri-substituted aziridines. This one-pot, two-step process involves formation of C-C and C-N bonds and subsequent cleavage of a C-N bond. The features of the developed reaction include the use of mild reaction conditions, broad substrate scope, and excellent yields. The synthetic utility of this approach was demonstrated by gram-scale operation and further product derivatizations.
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| http://dx.doi.org/10.1039/d4ra02817a | DOI Listing |
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