4.4 Article

Efficient Access to cis-Hydrobenzo[b]oxepines: Rhodium(l)-Catalyzed Cyclization of Cyclohexadienone-Tethered o-Tolyl-Substituted Alkynes

Journal

SYNLETT
Volume 29, Issue 9, Pages 1223-1228

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/S-0036-1591956

Keywords

rhodium catalysis; benzoxepines; enynes; cyclization; 1,4-rhodium shift

Funding

  1. 973 Program [2015CB856600]
  2. NSFC [21572251, 21572253, 21772063]
  3. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)

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An efficient access to cis-hydrobenzo[b]oxepine frameworks has been established through rhodium(l)-catalyzed cyclization of cyclo-hexadienone-tethered o-tolyl-substituted alkynes (1,6-enynes). The cascade process involves regioselective alpha-arylrhodation of the alkyne, 1,4-rhodium migration, and conjugate addition to cyclohexadienone.

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