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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 |
Appears in Collections: | Staff Publications Elements |
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[4] manuscript-Yu Zhao.pdf | Accepted version | 916.03 kB | Adobe PDF | OPEN | Post-print | View/Download |
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