MCM-41-Supported Linear Alkylamine-Catalyzed In Situ Generation of Unstable Trifluoroacetaldehyde and Successive syn-Selective Direct Aldol Reaction with Cyclic Ketones

被引：0

作者：

Funabiki, Kazumasa ^{[1
]}

Nagaya, Hideyuki ^{[1
]}

Gonda, Hiroshi ^{[1
]}

Sakaida, Yuta ^{[1
]}

Kubota, Yasuhiro ^{[1
]}

Matsui, Masaki ^{[1
]}

Kubota, Yoshihiro ^{[2
]}

机构：

[1] Gifu Univ, Dept Chem & Biomol Sci, 1-1 Yanagido, Gifu 5011193, Japan

[2] Yokohama Natl Univ, Div Mat Sci & Chem Engn, Hodogaya Ku, 79-5 Tokiwadai, Yokohama, Kanagawa 2408501, Japan

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 23期

基金：

日本学术振兴会;

关键词：

direct aldol reaction; MCM-41 supprted amine catalyst; syn-selective; trifluoroacetaldehyde; BETA-TRIFLUOROMETHYL KETONES; DIRECT ASYMMETRIC ALDOL; MESOPOROUS SILICA; ETHYL HEMIACETAL; MOLECULAR-SIEVES; ENANTIOSELECTIVE SYNTHESIS; CONDENSATION; PROLINE; ACID; ALUMINOSILICATE;

D O I：

10.1002/slct.201701093

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fixation of linear alkylamine on the ordered mesoporous silica (MCM-41) is effective on not only insitu generation of gaseous and unstable trifluoroacetaldehyde from its hemiacetal but also successive syn-selective direct aldol reaction with cyclohexanone giving the corresponding syn-aldol product. As results, the aldol product produced from cyclohexanone was obtained in good to excellent yield without the formation of a complex mixture, compared to our previous results with a mixture of catalysts such as organic amine/amorphous silica or organic amine/acetic acid. The obtained syn-selectivity is opposite to the L-proline derivatives-catalyzed anti-selective direct aldol reaction. Not only various aldehydes but also 1,3-dicarbonyl compounds, such as 2,4-pentandione and ethyl 3-oxobutanoate, are also participated in the MCM-41-supported N-methylpropylamine direct aldol reaction of CF3CHO hemiacetal, respectively.

引用

页码：6673 / 6682

页数：10

共 52 条

[1] L-Proline-Grafted Mesoporous Silica with Alternating Hydrophobic and Hydrophilic Blocks to Promote Direct Asymmetric Aldol and Knoevenagel-Michael Cascade Reactions [J].