Sterically Demanding Unsymmetrical Diaryl‐λ3‐iodanes for Electrophilic Pentafluorophenylation and an Approach to α‐Pentafluorophenyl Carbonyl Compounds with an All‐Carbon Stereocenter

ChemistryOpen

Kohei Matsuzaki¹  Kenta Okuyama¹  Etsuko Tokunaga¹  Dr. Motoo Shiro² 

[1] Department of Nanopharmaceutical Science & Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: [phone];Rigaku Corporation, 3-9-12 Mastubara-cho, Akishima, Tokyo 196-8666 (Japan)

关键词: asymmetric organocatalysis;    diaryl-λ3-iodanes;    electrophilic pentafluorophenylation;    palladium;   

DOI  :  10.1002/open.201402045

来源: Wiley

【 摘 要 】

Abstract

A sterically demanding unsymmetrical pentafluorophenyl-triisopropylphenyl-λ³-iodane was developed as an effective reagent for the electrophilic pentafluorophenylation of various β-keto esters and a β-keto amide. 17 examples of α-pentafluorophenylated 1,3-dicarbonyl compounds 3 having a quaternary carbon center are provided. The resulting compounds were nicely transformed into chiral α-pentafluorophenyl ketones with an all-carbon stereogenic center in high yields and high enantioselectivities using asymmetric organocatalysis (up to 98 % ee) or asymmetric metal catalysis (up to 82 % ee).

【 授权许可】

CC BY-NC   
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

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