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Catalysis and chemodivergence in the interrupted, formal homo-Nazarov cyclization using allylsilanes.

Authors
  • Shenje, Raynold1
  • Williams, Corey W
  • Francois, Katherine M
  • France, Stefan
  • 1 School of Chemistry and Biochemistry, Georgia Institute of Technology , Atlanta, Georgia 30332, United States. , (Georgia)
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Dec 19, 2014
Volume
16
Issue
24
Pages
6468–6471
Identifiers
DOI: 10.1021/ol503305r
PMID: 25495709
Source
Medline
License
Unknown

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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