Synthesis 2015; 47(19): 2937-2944
DOI: 10.1055/s-0034-1380452
special topic
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones

Kentaro Okuma*
Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan   Email: kokuma@fukuoka-u.ac.jp
,
Kenta Horigami
Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan   Email: kokuma@fukuoka-u.ac.jp
,
Noriyoshi Nagahora
Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan   Email: kokuma@fukuoka-u.ac.jp
,
Kosei Shioji
Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan   Email: kokuma@fukuoka-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 30 April 2015

Accepted after revision: 24 May 2015

Publication Date:
17 July 2015 (eFirst)

Abstract

The reaction of 2-(trimethylsilyl)phenyl triflate with aroyl­acetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselective oxidation of 4-aryl-2-naphthols with a chiral tridentate oxovanadium(IV) complex furnished the corresponding 4,4′-biaryl-1,1′-binaphthols in good yields.

Supporting Information

 
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