4.8 Article

Asymmetric Synthesis of Chiral 9,10-Dihydrophenanthrenes Using Pd-Catalyzed Asymmetric Intramolecular Friedel-Crafts Allylic Alkylation of Phenols

Journal

ORGANIC LETTERS
Volume 14, Issue 9, Pages 2350-2353

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol300770w

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Funding

  1. Ministry of Education, Culture, Sports, Science, and Technology, Japan
  2. Research Foundation for Pharmaceutical Sciences
  3. Grants-in-Aid for Scientific Research [23390003] Funding Source: KAKEN

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We developed a novel asymmetric synthetic method for multisubstituted 9,10-dihydrophenanthrenes based on the Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols, which produces 10-vinyl or 10-isopropenyl chiral 9,10-dihydrophenanthrene derivatives in high yield with up to 94% ee.

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