L-Proline and thiourea co-catalyzed condensation of acetone

被引：13

作者：

Xu, Lin ^{[1
,2
,3
]}

Wang, Fang ^{[4
]}

Huang, Jiejun ^{[2
,3
]}

Yang, Chenggen ^{[3
]}

Yu, Lei ^{[1
,2
,3
]}

Fan, Yining ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Key Lab Mesoscop Chem MOE, Nanjing 210093, Jiangsu, Peoples R China

[2] Jiangsu Yangnong Chem Grp Co Ltd, Yangzhou 225009, Jiangsu, Peoples R China

[3] Yangzhou Univ, Sch Chem & Chem Engn, Jiangsu Coinnovat Ctr Prevent & Control Important, Yangzhou 225002, Jiangsu, Peoples R China

[4] Yangzhou Polytechnol Inst, Yangzhou 225127, Jiangsu, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 27-28期

基金：

中国国家自然科学基金;

关键词：

Organocatalysis; Acetone condensation; L-Proline; Thiourea; Green synthesis; BAEYER-VILLIGER OXIDATION; ALPHA; BETA-UNSATURATED KETONES; FACILE ACCESS; ALDEHYDES; DERIVATIVES; 2-METHYLENECYCLOBUTANONES; ORGANOCATALYSIS; CYCLOBUTANONE; DEHYDRATION; ALDOXIMES;

D O I：

10.1016/j.tet.2016.05.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amino acid and primary amine amide co-catalyzed acetone condensation was investigated. It was found that L-proline had overwhelming catalytic activity over other amino acids as well as the analogues with similar structures. Surprisingly, thiourea, a very cheap and stable chemical, was found to be the favorable co-catalyst. Co-catalyzed by the recyclable L-proline and thiourea, condensation of acetone led to the useful products mesityl oxide (MO), diacetone alcohol (DAA) and isophorone (IP) in the excellent 96.3% total selectivity. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：4076 / 4080

页数：5

共 50 条

[1] l-proline and l-histidine co-catalyzed Baylis–Hillman reaction
Peng-Fei Guo
Qing-Yi Wei
Hong Jiang
Peng-Fei Xie
[J]. Research on Chemical Intermediates, 2012, 38 : 639 - 644
[2] Direct asymmetric aldol reaction co-catalyzed by L-proline and isothiouronium salts
Cho, Eun
Kim, Taek Hyeon
[J]. TETRAHEDRON LETTERS, 2014, 55 (47) : 6470 - 6473
[3] l-proline and l-histidine co-catalyzed Baylis-Hillman reaction
Guo, Peng-Fei
Wei, Qing-Yi
Jiang, Hong
Xie, Peng-Fei
[J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (02) : 639 - 644
[4] Green condensation reactions catalyzed by L-proline
Woods, J
Bennett, GD
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U403 - U403
[5] Lewis base and L-proline co-catalyzed Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone
Shi, M
Jiang, JK
Li, CQ
[J]. TETRAHEDRON LETTERS, 2002, 43 (01) : 127 - 130
[6] Direct asymmetric aldol reaction co-catalyzed by L-proline and group 12 elements Lewis acids in the presence of water
Penhoat, Mael
Barbry, Didier
Rolando, Christian
[J]. TETRAHEDRON LETTERS, 2011, 52 (01) : 159 - 162
[7] Asymmetric Aldol Reaction Catalyzed by L-Proline and Achiral Thiourea Fluoroboric Acid Salt
Cho, Eun
Lee, Haney
Kim, Taek Hyeon
[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (01): : 410 - 412
[8] L-Proline Catalyzed Multicomponent Reactions
Khandelwal, Sarita
Tailor, Yogesh Kumar
Kumar, Mahendra
[J]. CURRENT ORGANOCATALYSIS, 2016, 3 (02) : 176 - 204
[9] Liquid phase aldol condensation of formaldehyde and propionaldehyde catalyzed by L-proline functional polymers
Luo, Hongxian
Li, Gang
Ju, Longxin
Lv, Qiang
[J]. APPLIED CATALYSIS A-GENERAL, 2024, 670
[10] Addition of Acetone towards β-Cyano-α-oxoesters Catalyzed by L-Proline: Dynamic Kinetic Resolution
Wang Yajun
Zhang Yawen
[J]. CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (07) : 1267 - 1271

← 1 2 3 4 5 →