Wennemers Group (@wennemersgroup.bsky.social)

Chiral spirocyclic oxetanes & azetidines synthesized by organocatalytic additions to strained nitroolefins—a practical route to medicinally relevant molecules. 🔗 pubs.acs.org/doi/full/10....

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Enantioselective Conjugate Addition of Aldehydes to Oxetane- and Azetidine-Containing Nitroolefins: An Entry to Spirocyclic Pyrrolidines Enantioselective amine-catalyzed conjugate additions of aldehydes to oxetane- and azetidine-containing nitroolefins afford γ-nitroaldehydes as key building blocks en route to spirocyclic oxetane/azetidine-pyrrolidines. The study provided insights into the stability and reactivity of these β,β-disubstituted nitroolefins and enabled the enantioselective synthesis of chiral oxetanes and azetidines in moderate-to-high yields and enantioselectivities. This approach expands synthetic access to medicinally relevant scaffolds and broadens the scope of enantioselective organocatalytic transformations. https://pubs.acs.org/doi/full/10.1021/acs.orglett.5c00844