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 50 条

[1] Chiral pyrrolidine-azole conjugates: Simple and efficient asymmetric organocatalysts for Michael addition to nitrostyrenes
ZHANG Long XU Hui MI XueLing LUO SanZhong CHENG JinPei Department of Chemistry and State Key Laboratory of Elementoorganic Chemistry Nankai University Tianjin China Beijing National Laboratory for Molecular Sciences BNLMS CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences Beijing China
Chinese Science Bulletin, 2010, 55 (17) : 1735 - 1741
[2] Pyrrolidine based chiral organocatalyst for efficient asymmetric Michael addition of cyclic ketones to β-nitrostyrenes
Singh, Kamal Nain
Singh, Paramjit
Singh, Pushpinder
Lal, Nand
Sharma, Sandeep Kumar
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (13) : 4225 - 4228
[3] Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction
Mahato, Chandan K.
Mukherjee, Sayan
Kundu, Mrinalkanti
Pramanik, Animesh
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (02): : 1053 - 1063
[4] Chiral pyrrolidine quaternary derivatives as organocatalysts for asymmetric Michael additions
Sun, Huichao
Wang, Ge
Yan, Xilong
Chen, Ligong
RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (07) : 1501 - 1509
[5] Novel cyclic β-aminophosphonate derivatives as efficient organocatalysts for the asymmetric Michael addition reactions of ketones to nitrostyrenes
Widianti, Triana
Hiraga, Yoshikazu
Kojima, Satoshi
Abe, Manabu
TETRAHEDRON-ASYMMETRY, 2010, 21 (15) : 1861 - 1868
[6] Chiral pyrrolidine quaternary derivatives as organocatalysts for asymmetric Michael additions
Huichao Sun
Ge Wang
Xilong Yan
Ligong Chen
Research on Chemical Intermediates, 2012, 38 : 1501 - 1509
[7] Pyrrolidine-based chiral pyridinium ionic liquids (ILs) as recyclable and highly efficient organocatalysts for the asymmetric Michael addition reactions
Ni, Bukuo
Zhang, Qianying
Headley, Allan D.
TETRAHEDRON LETTERS, 2008, 49 (07) : 1249 - 1252
[8] Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to nitroolefins
Luo, Sanzhong
Mi, Xueling
Zhang, Long
Liu, Song
Xu, Hui
Cheng, Jin-Pei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) : 3093 - 3097
[9] Silica gel supported pyrrolidine-based chiral ionic liquid as recyclable organocatalyst for asymmetric Michael addition to nitrostyrenes
Li, Pinhua
Wang, Lei
Zhang, Yicheng
Wang, Guanwu
TETRAHEDRON, 2008, 64 (32) : 7633 - 7638
[10] Pyrrolidine modified PANF catalyst for asymmetric Michael addition of ketones to nitrostyrenes in aqueous phase
Du, Jianguo
Shuai, Bin
Tao, Minli
Wang, Guangwei
Zhang, Wenqin
GREEN CHEMISTRY, 2016, 18 (09) : 2625 - 2631

← 1 2 3 4 5 →