A Lewis‐Acid‐Catalyzed Phenolic Ether 'O to C' Rearrangement: Synthesis of 4‐Aryldihydrocoumarins. Issue 7 (20th May 2019)

• Record Type: Journal Article
• Authors: Kumar, Praveen; Kunkalkar, Rupesh A.; Fernandes, Rodney A.
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 7(2019)
• Page Start: 1001
• Page End: 1009
• Publication Date: 2019-05-20
• Subjects: Lewis acids -- rearrangement -- dihydrocoumarins -- bioactivity -- natural products; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900213
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: An efficient O to C rearrangement of phenolic ethers is developed. The Lewis acid BF3 ⋅OEt2 (0.5 equiv) could catalyze the O to C migration of β‐aryloxy‐β‐arylesters to β, β‐bis‐arylesters, thereby the free phenolic OH cyclizes with the ester group, resulting in the formation of 4‐aryldihydrocoumarins. Abstract : On Call: An efficient O to C rearrangement of β‐aryloxy‐β‐arylesters to β, β‐bis‐arylesters is described. The free phenolic OH group cyclizes with the ester, resulting in the formation of 4‐aryldihydrocoumarins.