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

Kentaro Okuma; Kenta Horigami; Noriyoshi Nagahora; Kosei Shioji

doi:10.1055/s-0034-1380452

Synthesis, Table of Contents

Synthesis 2015; 47(19): 2937-2944
DOI: 10.1055/s-0034-1380452

special topic

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

Authors

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

Abstract

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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.

Key words

aryne - β-diketone - carbon–carbon bond insertion - 4-aryl-2-naphthol - BINOL

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References

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