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Gao, S. et al.: 2016 Science of Synthesis, 2016/4b: Metal-Catalyzed Cyclization Reactions 2 DOI: 10.1055/sos-SD-222-00208
Metal-Catalyzed Cyclization Reactions 2

2.8 Metal-Catalyzed (5 + 1), (5 + 2), and (5 + 2 + 1) Cycloadditions

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Book

Editors: Gao, S.; Ma, S.

Authors: Bora, U.; Dominguez, G.; Du, H.; Garve, L.; Harmata, M.; Hu, W.; Jones, D. E.; Lee, D.; Li, X.; Mondal, M.; Pérez Castells, J.; Sabbasani, V. R.; Shibata, Y.; Tanaka, K.; Tang, W.; Werz, D. B.; Xia, F.; Xu, X.; Ye, S.

Title: Metal-Catalyzed Cyclization Reactions 2

Print ISBN: 9783131998118; Online ISBN: 9783132404823; Book DOI: 10.1055/b-004-129734

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

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

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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

Metal-catalyzed (5 + n) cycloaddition is a powerful strategy for the synthesis of six-, seven-, and eight-membered carbocycles and heterocycles. These cycloadditions usually involve oxidative cyclization to a metallacycle; insertion into the C—M bond (e.g., by carbon monoxide, an alkene, alkyne, or allene, or a combination thereof); and reductive elimination. Vinylcyclopropanes and 3-acyloxy-1,4-enynes are the most common five-carbon synthons. Recent advances in transition-metal-catalyzed (5 + 1), (5 + 2), and (5 + 2 + 1) cycloadditions including their development, mechanistic studies, and applications are reviewed in this chapter.

Key words

cycloaddition - transition metals - catalysis - vinylcyclopropanes - propargylic esters - (5 + 1) cycloaddition - (5 + 2) cycloaddition - (5 + 2 + 1) cycloaddition - carbocycles - heterocycles - seven-membered rings - alkenes - alkynes - allenes - imines - cyclopropanes - epoxides - rhodium - ruthenium - nickel - iron - dictamnol - aphanamol - allocyathin B2 - tremulenediol A - tremulenolide A - pseudolaric acid B - frondosin A - rameswaralide - hirsutene - desoxyhypnophilin - asteriscanolide
 
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