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  • Title: Catalysis and chemodivergence in the interrupted, formal homo-Nazarov cyclization using allylsilanes.
    Author: Shenje R, Williams CW, Francois KM, France S.
    Journal: Org Lett; 2014 Dec 19; 16(24):6468-71. PubMed ID: 25495709.
    Abstract:
    A chemodivergent, Lewis acid catalyzed allylsilane interrupted formal homo-Nazarov cyclization is disclosed. With catalytic amounts of SnCl4 and in the presence of allyltrimethylsilane, a formal Hosomi-Sakurai-type allylation of the oxyallyl cation intermediate is observed. A variety of functionalized donor-acceptor cyclopropanes and allylsilanes were shown to be amenable to the reaction transformation and the allyl products were formed in up to 92% yield. Under dilute reaction conditions with stoichiometric SnCl4 and at reduced temperatures, an unusual formal [3 + 2]-cycloaddition between the allylsilane and the oxyallyl cation occurred to give hexahydrobenzofuran products in up to 69% yield.
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