Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.201801768
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dc.titleDivergent, Enantioselective Synthesis of Pyrroles, 3H-Pyrroles and Bicyclic Imidazolines by Ag- or P-Catalyzed [3+2] Cycloaddition of Allenoates with Activated Isocyanides
dc.contributor.authorKok, Germaine Pui Yann
dc.contributor.authorShao, Pan-Lin
dc.contributor.authorLiao, Jia-Yu
dc.contributor.authorIsmail, Siti Nur Fairuz Bte Sheikh
dc.contributor.authorYao, Weijun
dc.contributor.authorYixin, Lu
dc.contributor.authorZhao, Yu
dc.date.accessioned2020-06-18T02:12:52Z
dc.date.available2020-06-18T02:12:52Z
dc.date.issued2018-07-20
dc.identifier.citationKok, Germaine Pui Yann, Shao, Pan-Lin, Liao, Jia-Yu, Ismail, Siti Nur Fairuz Bte Sheikh, Yao, Weijun, Yixin, Lu, Zhao, Yu (2018-07-20). Divergent, Enantioselective Synthesis of Pyrroles, 3H-Pyrroles and Bicyclic Imidazolines by Ag- or P-Catalyzed [3+2] Cycloaddition of Allenoates with Activated Isocyanides. CHEMISTRY-A EUROPEAN JOURNAL 24 (41) : 10513-10520. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.201801768
dc.identifier.issn0947-6539,1521-3765
dc.identifier.urihttps://scholarbank.nus.edu.sg/handle/10635/170268
dc.description.abstract© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The divergent, stereoselective formal [3+2] cycloadditions of allenoates with activated isocyanides catalyzed by silver or phosphine-based catalysts were investigated. Silver catalysis is capable of delivering a range of 3H-pyrroles in high stereoselectivities. These enantioenriched heterocycles can either undergo sequential cyclisation with isocyanoacetates to deliver unprecedented bicyclic imidazolines with excellent yields and stereoselectivity or undergo unusual aromatization pathways leading to polysubstituted pyrroles. On the other hand, a simple mix-and-go procedure using an amino acid-derived phosphine as the catalyst produces pyrroles bearing a benzylic stereocenter with good enantioselectivity.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.sourceElements
dc.subjectScience & Technology
dc.subjectPhysical Sciences
dc.subjectChemistry, Multidisciplinary
dc.subjectChemistry
dc.subjectcycloaddition
dc.subjectenantioselectivity
dc.subjectimidazolines
dc.subjectphosphine catalysis
dc.subjectpyrroles
dc.subjectsilver catalysis
dc.subjectASYMMETRIC ALDOL REACTION
dc.subjectCHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX
dc.subjectDIASTEREOSELECTIVE MANNICH REACTION
dc.subjectALPHA-SUBSTITUTED ISOCYANOACETATES
dc.subjectOLIGOSUBSTITUTED PYRROLES
dc.subjectQUATERNARY STEREOCENTERS
dc.subjectMULTICOMPONENT SYNTHESIS
dc.subjectN-SULFONYLIMINES
dc.subjectMICHAEL ADDITION
dc.subjectCYCLIZATION
dc.typeArticle
dc.date.updated2020-06-17T04:15:37Z
dc.contributor.departmentDEPT OF CHEMISTRY
dc.description.doi10.1002/chem.201801768
dc.description.sourcetitleCHEMISTRY-A EUROPEAN JOURNAL
dc.description.volume24
dc.description.issue41
dc.description.page10513-10520
dc.published.statePublished
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