Abstract
AbstractIn the present work, we report the addition reactions between (S)‐ and (R)‐N‐t‐butylsulfinyl‐3,3,3‐trifluoro‐acetaldimine and tertiary enolates derived from α‐thiocyanate ketones. We demonstrate that these reactions feature unusual regiodivergence, affording either the direct Mannich adducts (NaOAc/THF) or the products of tandem Mannich addition‐cyclization (Na2CO3/DMF) reactions. The latter represents a new class of spirocyclic trifluoromethyl‐containing aziridines unavailable by other approaches. The reactions show wide structural generality, rendering them of certain synthetic value for preparation of new fluorine‐containing polyfunctional compounds of biological relevance. Mechanistic rationale for the observed reactivity and stereochemical outcome is provided.magnified image
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