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

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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