ChemistryOpen | |
Sterically Demanding Unsymmetrical Diaryl‐λ3‐iodanes for Electrophilic Pentafluorophenylation and an Approach to α‐Pentafluorophenyl Carbonyl Compounds with an All‐Carbon Stereocenter | |
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: (+81) 527357543;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 】
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).Abstract
【 授权许可】
CC BY-NC
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
【 预 览 】
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RO202107150004473ZK.pdf | 388KB | download |