4.7 Article

Facially Selective Cu-Catalyzed Carbozincation of Cyclopropenes Using Arylzinc Reagents Formed by Sequential I/Mg/Zn Exchange

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 21, Pages 9900-9904

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo3019076

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Funding

  1. NIGMS [NIH R01 GM068650]
  2. NSF CRIF:MU [CHE 0840401, CHE-0541775]

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Described is a Cu-catalyzed directed carbozincation of cyclopropenes with organozinc reagents prepared by I/Mg/Zn exchange. This protocol broadens the scope with respect to functional group tolerance and enables use of aryl iodide precursors, rather than purified diorganozinc precursors. Critical to diastereoselectivity of the carbozincation step is the removal of magnesium halide salts after transmetalation with ZnCl2.

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