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Gao, S. et al.: 2016 Science of Synthesis, 2016/4a: Metal-Catalyzed Cyclization Reactions 1 DOI: 10.1055/sos-SD-221-00172
Metal-Catalyzed Cyclization Reactions 1

1.6 Metal-Catalyzed Cyclization Reactions of Allenes

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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

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Abstract

Allenes represent a unique scaffold for powerful cyclization reactions due to the ability to incorporate additional functionality into the newly formed ring. Metal-catalyzed cyclization reactions of allenes represent a powerful strategy for the synthesis of highly functionalized heterocycles and carbocycles. A variety of metals can be used to facilitate cyclization; the nature of the metal influences which allene carbon is attacked by an internal nucleophile, leading to convenient access to multiple ring systems from a simple precursor. The unique axial chirality of allenes can dictate the stereochemistry featured in the ring through axial-to-point chirality transfer.

Key words

allenes - chirality transfer - carbocycles - heterocycles - pyrrolidines - benzocycles - cyclopropanes
 
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