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Home  > Press Release  > Synthesis of Diverse γ-Aryl-β-ketoesters via Aryne Intermediates Generated by C–C Bond Cleavage

Synthesis of Diverse γ-Aryl-β-ketoesters via Aryne Intermediates Generated by C–C Bond Cleavage

Abstract

A synthetic method for diverse γ-aryl-β-ketoesters through γ-aryl-β-ketoester-type arynes triggered by C–C bond cleavage has been developed. The Mukaiyama aldol reaction of 6-(triflyloxy)benzocyclobutenones with ketene silyl acetals and subsequent treatment of resulting 6-(triflyloxy)benzocyclobutenols with a base triggered the efficient generation of γ-aryl-β-ketoester-type arynes, which reacted with various arynophiles to provide a wide range of γ-aryl-β-ketoesters. The synthetic utility of the method was demonstrated by the synthesis of an analog of ALK inhibitor.

Journal Article

JOURNAL:
Organic Letters

TITLE:
Synthesis of Diverse γ-Aryl-β-ketoesters via Aryne Intermediates Generated by C–C Bond Cleavage

DOI:
http://dx.doi.org/10.1021/acs.orglett.9b03418

Correspondence to

Takamitsu HOSOYA, Professor
Department of Chemical Bioscience,
Institute of Biomaterials and Bioengineering,
Tokyo Medical and Dental University(TMDU)
E-mail:thosoya.cb(at)tmd.ac.jp


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