Electrophilic 1,4-Addition of Carbon Dioxide and Aldehydes to Enones

被引：4
作者：
Okumura, Shintaro [1 ]
Torii, Kaoru [1 ]
Uozumi, Yasuhiro [1 ]
机构：
[1] Inst Mol Sci, Okazaki 4448787, Japan
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 28期
关键词：
ALPHA; BETA-UNSATURATED KETONES; TETRAHYDROFURAN; HOMOENOLATE; GENERATION;
D O I：
10.1021/acs.orglett.3c01675
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An umpoled electrophilic 1,4-addition to enones was achievedunderphotocatalytic conditions. Various enones reacted with CO2 in the presence of an iridium photocatalyst and a benzimidazolinereductant under blue-light irradiation to give the corresponding & gamma;-ketocarboxylic acids. Aldehydes also coupled with enones under similarphotocatalytic conditions to afford & gamma;-keto alcohols (homoaldols)that were transformed into dihydrofurans and tetrahydrofurans throughazeotropic posttreatments. Regioselective deuterium incorporationfrom D2O at the & beta;-position demonstrated that 1,4-additiontakes place via homoenolate anions.
引用
收藏
页码：5226 / 5230
页数：5
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