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Although π-allyl chemistry is a cornerstone of catalysis, allylic substitution with unstabilized (“hard”) organometallic nucleophiles has not previously been reviewed as a unified field. This review fills that gap. We survey aryl, alkyl, allyl, alkenyl, alkynyl, benzyl, and allenyl reagents across achiral, stereoselective, and stereospecific processes, highlighting mechanistic insight and reaction design that enable control in these challenging transformations.
Debasis Pal, Kirana D. Veeranna, and P. Andrew Evans, "Advances in Transition Metal-Catalyzed Allylic Substitution with Unstabilized Nucleophiles", Sci China Chem, 2026, 69(1), 94-118.
Yu Zhu and P. Andrew Evans, 6.09 Higher Order Cycloadditions, Editor(s): Paul Knochel, Comprehensive Organic Synthesis (Third Edition), Elsevier, 2025, Pages 545–596.
We’ve developed a practical, transition-metal-free, enantiospecific alkylation that allows unactivated secondary electrophiles to participate cleanly and predictably—an outcome long viewed as challenging. The reaction is operationally straightforward, uses readily available building blocks, and delivers enantioenriched α-tertiary ketones with high stereochemical fidelity and broad functional-group tolerance. By rethinking how cyanohydrins function as nucleophiles, this work invites a reassessment of the scope of SN2 chemistry, while remaining firmly grounded in everyday synthetic practice.
Jinjin Ma, Hui Li, Jadab Majhi, and P. Andrew Evans, "Stereospecific Transition-Metal-Free Alkylation of Chiral Non-Racemic Secondary Tosylates with Cyanohydrins: Convenient Access to Enantiomerically Enriched α-Tertiary Ketones, Angew. Chem. Int. Ed. 2025, e20674
