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Unexpected Selectivity of Intramolecular [3+2] Cycloaddition of Trimethylenemethane (TMM) Diyl toward Total Synthesis of Conidiogenone B

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Title
Unexpected Selectivity of Intramolecular [3+2] Cycloaddition of Trimethylenemethane (TMM) Diyl toward Total Synthesis of Conidiogenone B
Author(s)
Myungjo J. Kim; Lee Snaghyeon; Kang Taek; Baik Mu-Hyun; Lee Hee-Yoon
Subject
Natural products, ; Total synthesis, ; Regioselectivity, ; Radicals, ; Density functional calculations
Publication Date
2020-02
Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2020, no.5, pp.609 - 617
Publisher
WILEY-V C H VERLAG GMBH
Abstract
In the course of a study toward a total synthesis of conidiogenone B through TMM diyl-mediated tandem cycloaddition reaction, unexpected regioselectivity for a bridged isomer was observed. The synthetic and computational studies with model compounds revealed that regioselectivity can be rendered by changing substitution patterns on the TMM diyl moiety and the olefin moiety by altering the activation energy of cycloaddition reaction through a singlet TMM diyl pathway © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/7012
DOI
10.1002/ejoc.201901700
ISSN
1434-193X
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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