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Gao, S. et al.: 2016 Science of Synthesis, 2016/4a: Metal-Catalyzed Cyclization Reactions 1 DOI: 10.1055/sos-SD-221-00093
Metal-Catalyzed Cyclization Reactions 1

1.4 Metal-Catalyzed Intramolecular Cyclizations Involving Cyclopropane and Cyclopropene Ring Opening

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Book

Editors: Gao, S.; Ma, S.

Authors: Alderson, J.; Beccalli, E. M.; Bonetti, A.; Gao, S.; Guiry, P.; Jammi, S.; Mazza, A.; Nottingham, C.; Phelps, A.; Schomaker, J. M.; Shi, M.; Tang, X.-Y.; Wang, D.; Yamamoto, Y.; You, S. ; Zhang, L.; Zhang, X.

Title: Metal-Catalyzed Cyclization Reactions 1

Print ISBN: 9783131998613; Online ISBN: 9783132403406; Book DOI: 10.1055/b-003-129294

1st edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

Also available at
 


Abstract

Due to the ring strain of cyclopropane rings, transition-metal catalysts can easily undergo an oxidative addition with the cyclopropane moiety of methylenecyclopropanes (MCPs) to give trimethylenemethane (TMM) intermediates. Subsequent intramolecular cyclization with unsaturated systems takes place to give cyclized products. Moreover, in the presence of a chiral ligand, high enantioselectivity can be achieved. The ring-fused products are versatile building blocks in organic synthesis.

Key words

cyclopropanes - methylenecyclopropanes - ring-opening reactions - cyclization - alkenes - alkynes - transition-metal catalysts - trimethylenemethanes - palladium - nickel - rhodium - ruthenium - chiral synthesis
 
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