Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.201801768
Title: Divergent, Enantioselective Synthesis of Pyrroles, 3H-Pyrroles and Bicyclic Imidazolines by Ag- or P-Catalyzed [3+2] Cycloaddition of Allenoates with Activated Isocyanides
Authors: Kok, Germaine Pui Yann
Shao, Pan-Lin
Liao, Jia-Yu
Ismail, Siti Nur Fairuz Bte Sheikh
Yao, Weijun 
Yixin, Lu 
Zhao, Yu 
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
cycloaddition
enantioselectivity
imidazolines
phosphine catalysis
pyrroles
silver catalysis
ASYMMETRIC ALDOL REACTION
CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX
DIASTEREOSELECTIVE MANNICH REACTION
ALPHA-SUBSTITUTED ISOCYANOACETATES
OLIGOSUBSTITUTED PYRROLES
QUATERNARY STEREOCENTERS
MULTICOMPONENT SYNTHESIS
N-SULFONYLIMINES
MICHAEL ADDITION
CYCLIZATION
Issue Date: 20-Jul-2018
Publisher: WILEY-V C H VERLAG GMBH
Citation: Kok, 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
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.
Source Title: CHEMISTRY-A EUROPEAN JOURNAL
URI: https://scholarbank.nus.edu.sg/handle/10635/170268
ISSN: 0947-6539,1521-3765
DOI: 10.1002/chem.201801768
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