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Efficient Catalytic Asymmetric Synthesis of trans ‐5‐Aryl‐2‐substituted Cyclohexanones by Rhodium‐Catalyzed Conjugate Arylation of Racemic 6‐Substituted Cyclohexenones
Author(s) -
Chen Qian,
Soeta Takahiro,
Kuriyama Masami,
Yamada Kenichi,
Tomioka Kiyoshi
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600263
Subject(s) - chemistry , catalysis , conjugate , aryl , rhodium , sodium ethoxide , ethanol , medicinal chemistry , enantioselective synthesis , organic chemistry , mathematical analysis , alkyl , mathematics
Catalytic asymmetric conjugate arylation of racemic 6‐substituted cyclohexenones with arylboronic acids was catalyzed by 3 mol % of chiral amidophosphane‐[RhCl(C 2 H 4 )] 2 in a 10:1 mixture of 1,4‐dioxane and water at 70 °C to afford a nearly 1:1 mixture of trans ‐ and cis ‐5‐aryl‐2‐substituted cyclohexanones in high enantioselectivity, which was subsequently epimerized with sodium ethoxide in ethanol to give thermodynamically stable trans ‐5‐aryl‐2‐substituted cyclohexanones with 99–97 % ee in high two‐step yields.