4.8 Article

Oxidative Cyclization of Sulfamates onto Pendant Alkenes

Journal

ORGANIC LETTERS
Volume 22, Issue 3, Pages 896-901

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04448

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Funding

  1. University of Kansas Office of the Provost
  2. Department of Medicinal Chemistry
  3. COBRE Protein Structure and Function Small Grants Program
  4. NIH Shared Instrumentation Grant [S10RR014767]

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This communication discloses the first examples of aza-Wacker cyclizations of sulfamate esters. Within the realm of related cyclization reactions, this protocol is differential in that it forms six-membered rings in good yield and uses catalytic amounts of palladium(0) rather than palladium(II) salts. These reactions scale well, and their products are demonstrated to be valuable synthetic intermediates.

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