Palladium
and Lewis-Acid-Catalyzed Intramolecular
Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene
Difunctionalizations
Posted on 2018-02-20 - 21:18
An expansion of methodologies aimed
at the formation of versatile
organonitriles, via the intramolecular aminocyanation of unactivated
alkenes, is herein reported. Importantly, the need for a rigid tether
in these reactions has been obviated. The ease-of-synthesis and viability
of substrates bearing flexible backbones has permitted for diastereoselective
variants as well. We demonstrated the utility of this methodology
with the formation of pyrrolidones, piperidinones, isoindolinones,
and sultams. Furthermore, subsequent transformation of these motifs
into medicinally relevant molecules is also demonstrated. A double
crossover 13C-labeling experiment is consistent with a
fully intramolecular cyclization mechanism. Deuterium labeling experiments
support a mechanism involving syn-addition across
the alkene.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Pan, Zhongda; Wang, Shengyang; Brethorst, Jason T.; Douglas, Christopher J. (2018). Palladium
and Lewis-Acid-Catalyzed Intramolecular
Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene
Difunctionalizations. ACS Publications. Collection. https://doi.org/10.1021/jacs.8b01330
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
AUTHORS (4)
ZP
Zhongda Pan
SW
Shengyang Wang
JB
Jason T. Brethorst
CD
Christopher J. Douglas
KEYWORDS
motifpiperidinoneexperiments supportcrossover 13 C-labeling experimentMechanismLewis-Acid-Catalyzed Intramolecular AminocyanationisoindolinoneScopetetherutilityviabilitymethodologyImportantlyunactivated alkenesStereoselective Alkene DifunctionalizationsPalladiumintramolecular aminocyanationpyrrolidonemedicinallymoleculesynDeuteriumformationsubstratetransformationintramolecular cyclization mechanismorganonitrilesultamease-of-synthesiobviateddiastereoselective variants