NDLI: General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides and Lactams.

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General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides and Lactams.

Content Provider	Europe PMC
Author	Yamazaki, Ken Gabriel, Pablo Di Carmine, Graziano Pedroni, Julia Farizyan, Mirxan Hamlin, Trevor A. Dixon, Darren J.
Copyright Year	2021
Abstract	Aniridium-catalyzed reductive generation of both stabilized andunstabilized azomethine ylides and their application to functionalizedpyrrolidine synthesis via [3 + 2] dipolar cycloaddition reactionsis described. Proceeding under mild reaction conditions from bothamide and lactam precursors possessing a suitably positioned electron-withdrawingor a trimethylsilyl group, using 1 mol% Vaska’s complex [IrCl(CO)(PPh3)2] and tetramethyldisiloxane (TMDS) as a terminalreductant, a broad range of (un)stabilized azomethine ylides wereaccessible. Subsequent regio- and diastereoselective, inter- and intramoleculardipolar cycloaddition reactions with variously substituted electron-deficientalkenes enabled ready and efficient access to structurally complexpyrrolidine architectures. Density functional theory (DFT) calculationsof the dipolar cycloaddition reactions uncovered an intimate balancebetween asynchronicity and interaction energies of transition structures,which ultimately control the unusual selectivities observed in certaincases.
Related Links	https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC8291578&blobtype=pdf
Journal	ACS Catalysis [ACS Catal]
Volume Number	11
DOI	10.1021/acscatal.1c01589
PubMed Central reference number	PMC8291578
Issue Number	12
PubMed reference number	34306810
e-ISSN	21555435
Language	English
Publisher	American ChemicalSociety
Publisher Date	2021-06-09
Access Restriction	Open
Rights License	Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). © 2021 AmericanChemical Society
Subject Keyword	Vaska’s complex amide reduction [3+ 2] cycloaddition azomethine ylide pyrrolidines polycyclic amine density functional calculations
Content Type	Text
Resource Type	Article
Subject	Chemistry Catalysis

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