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Issue 9, 2014
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Allene ether Nazarov cyclization

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The ease of synthesis and the exceptional reactivity of alkoxyallenes has led to their use in a large number of highly diverse applications. This Report describes their use in various versions of the allene ether Nazarov cyclization. Following a brief introduction to the Nazarov cyclization (Section 1), the oxidative cyclization of vinyl alkoxyallenes is discussed first (Section 2). Nazarov cyclizations of α-alkoxyallenyl vinyl ketones and of α-alkoxyallenyl vinyl tertiary carbinols are covered (Section 3). The discovery and the subsequent rational design of acetals that serve as chiral auxiliaries on the allene in highly enantioselective Nazarov cyclizations is explained (Section 4). Interrupted Nazarov cyclizations of alkoxyallenes that are generated in situ from the isomerization of propargyl ethers on solid supports are discussed, including the evolution of a highly diastereoselective, chiral auxiliary controlled version of the reaction. Some applications of the methodology to natural products total synthesis have been included so as to provide the reader with benchmarks with which to judge the utility of the methodology.

Graphical abstract: Allene ether Nazarov cyclization

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The article was received on 19 Sep 2013 and first published on 06 Nov 2013

Article type: Review Article
DOI: 10.1039/C3CS60333D
Chem. Soc. Rev., 2014,43, 2979-3002

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    Allene ether Nazarov cyclization

    M. A. Tius, Chem. Soc. Rev., 2014, 43, 2979
    DOI: 10.1039/C3CS60333D

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