Enantioselective CH Bond Functionalization Triggered by Radical Trifluoromethylation of Unactivated Alkene

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書誌事項

公開日
2014-09-08
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
  • http://doi.wiley.com/10.1002/tdm_license_1.1
DOI
  • 10.1002/anie.201405401
公開者
Wiley

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説明

<jats:title>Abstract</jats:title> <jats:p> An asymmetric unactivated alkene/CH bond difunctionalization reaction for the concomitant construction of CCF <jats:sub>3</jats:sub> and CO bonds was realized by using a Cu/Brønsted acid cooperative catalytic system, thus providing facile access to valuable chiral CF <jats:sub>3</jats:sub> ‐containing N,O‐aminals with excellent regio‐, chemo‐, and enantioselectivity. Mechanistic studies revealed that this reaction may proceed by an unprecedented 1,5‐hydride shift involving activation of unactivated alkenes and a radical trifluoromethylation to initiate subsequent enantioselective functionalization of CH bonds. Control experiments also suggested that chiral Brønsted acid plays multiple roles and not only controls the stereoselectivity but also increases the reaction rate through activation of Togni’s reagent. </jats:p>

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