4.8 Article

Enantioselective Friedel-Crafts Alkylation of Furans with o-Quinone Methide Using a Chiral Oxazaborolidinium Ion Catalyst

Journal

ORGANIC LETTERS
Volume 24, Issue 8, Pages 1732-1736

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00404

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Funding

  1. National Research Foundation of Korea [NRF-2019R1A2C2087018]
  2. Korean Government (MSIT)
  3. 111 Project [D18012]

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A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts alkylation using in situ-generated o-quinone methides has been developed. The reaction showed high yield (up to 99%) and excellent enantioselectivity (up to >99% ee) in the presence of a chiral oxazaborolidinium ion catalyst.
A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts loran alkylation with in situ-generated o-quinone methides has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99%) with excellent enantioselectivity (up to >99% ee).

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