Abstract
AbstractCommercially available iron(III) and copper(I) complexes catalyzed multicomponent cycloaddition reactions between diazo compounds, pyridines, and electrophilic alkenes to give alkaloid‐inspired tetrahydroindolizidines in high yield with high diastereoselectivity. Hitherto, the catalytic formation of versatile pyridinium ylides from metal carbenes has been poorly developed; the broad utility demonstrated herein sets the stage for the invention of further multicomponent reactions in future.
Highlights
Convergent synthesis of tetrahydroindolizidines can be achieved by 1,3-dipolar cycloaddition of pyridinium ylides with electrophilic alkenes
Pyridinium ylides are formed by deprotonation of the corresponding salts but this protocol produces stoichiometric conjugate acid waste and usually requires a separate alkylation step to prepare the pyridinium salts
The addition of Lewis bases to metal carbenes to form ylides has been widely developed for synthesis,[13,14,15,16,17,18,19,20] but there are few reports of catalysed reactions of pyridines with diazo compounds.[21,22]
Summary
Convergent synthesis of tetrahydroindolizidines can be achieved by 1,3-dipolar cycloaddition of pyridinium ylides with electrophilic alkenes. We describe a new, multicomponent reaction that produces highly functionalized tetrahydroindolizidines in good yields with generally excellent diastereoselectivities (Scheme 2).
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