Open AccessSterically Demanding Unsymmetrical Diaryl‐λ 3 ‐iodanes for Electrophilic Pentafluorophenylation and an Approach to α‐Pentafluorophenyl Carbonyl Compounds with an All‐Carbon Stereocenter
Author(s) -
Matsuzaki Kohei,
Okuyama Kenta,
Tokunaga Etsuko,
Shiro Motoo,
Shibata Norio
Publication year - 2014
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201402045
Subject(s) - stereocenter , electrophile , chemistry , steric effects , organocatalysis , reagent , amide , catalysis , organic chemistry , carbon fibers , enantioselective synthesis , combinatorial chemistry , medicinal chemistry , materials science , composite number , composite material
A sterically demanding unsymmetrical pentafluorophenyl‐triisopropylphenyl‐λ 3 ‐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 ).