Chiral pyrrolidine-azole conjugates: Simple and efficient asymmetric organocatalysts for Michael addition to nitrostyrenes

被引：3

作者：

Zhang Long ^{[2
,3
]}

Xu Hui ^{[1
]}

Mi XueLing ^{[2
,3
]}

Luo SanZhong ^{[1
]}

Cheng Jin-Pei ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, BNLMS, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China

[2] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China

[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

CHINESE SCIENCE BULLETIN | 2010年 / 55卷 / 17期

基金：

中国国家自然科学基金;

关键词：

pyrrolidine; azole; organocatalysis; Michael addition; nitrostyrene; CLICK CHEMISTRY; ENANTIOSELECTIVE ADDITION; CYCLIC-KETONES; NITRO-MICHAEL; IONIC LIQUIDS; ALDEHYDES; CATALYSTS; PROLINE; NITROALKENES; CYCLOHEXANONE;

D O I：

10.1007/s11434-010-3120-9

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Simple pyrrolidine-azole conjugates have been synthesized and found to be efficient catalysts for asymmetric Michael addition to nitrostyrenes. The identified optimal catalysts, pyrrolidine-azoles 2, 8 and 13, could catalyze the asymmetric Michael addition of a range of Michael donors and nitrostyrenes in high yields (up to 99%) and excellent stereoselectivities (up to 99: 1 dr and 97% ee).

引用

页码：1735 / 1741

页数：7

共 63 条

[1] Amine-catalyzed Michael reactions of an aminoaldehyde derivative to nitroolefins
Albertshofer, Klaus
Thayumanavan, Rajeswari
Utsumi, Naoto
Tanaka, Fujie
Barbas, Carlos F., III
[J]. TETRAHEDRON LETTERS, 2007, 48 (04) : 693 - 696
[2] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
Alexakis, A
Andrey, O
[J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
[3] Enantioselective conjugate addition of ketones to β-nitrostyrenes catalyzed by 1,2-amino alcohol-derived prolinamides
Almasi, Diana
Alonso, Diego A.
Najera, Carmen
[J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (14) : 2064 - 2068
[4] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins
Andrey, O
Alexakis, A
Tomassini, A
Bernardinelli, G
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1147 - 1168
[5] Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin
Andrey, O
Vidonne, A
Alexakis, A
[J]. TETRAHEDRON LETTERS, 2003, 44 (43) : 7901 - 7904
[6] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine
Andrey, O
Alexakis, A
Bernardinelli, G
[J]. ORGANIC LETTERS, 2003, 5 (14) : 2559 - 2561
[7] Chiral piperazines as efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes
Barros, Maria Teresa
Phillips, Ana Maria Faisca
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) : 178 - 185
[8] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[9] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
Betancort, JM
Barbas, CF
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
[10] Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins
Cao, Chun-Li
Ye, Meng-Chun
Sun, Xiu-Li
Tang, Yong
[J]. ORGANIC LETTERS, 2006, 8 (14) : 2901 - 2904

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