Epiandrosterone-derived prolinamide as an efficient asymmetric catalyst for Michael addition reactions of aldehydes to nitroalkenes

被引：17

作者：

Wang, Yongchao ^{[1
]}

Ji, Shen ^{[1
]}

Wei, Kun ^{[1
]}

Lin, Jun ^{[1
]}

机构：

[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 58期

关键词：

DOMINO REACTIONS; SILYL ETHERS; ORGANOCATALYSTS; CONSTRUCTION; KETONES; DERIVATIVES; CASCADE; ACID;

D O I：

10.1039/c4ra03075c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Epiandrosterone derivatives-organocatalyzed asymmetric Michael addition of aldehydes to nitroalkenes was investigated. Among the various catalysts, a novel type of epiandrosterone-derived L-prolineamide catalyst was synthesized and exhibited better performance in both catalytic activity and stereoselectivity, providing the products with high yields (up to 98%), excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99 : 1 dr), and low catalyst loading (5 mol%).

引用

页码：30850 / 30856

页数：7

共 50 条

[41] Solid supported Hayashi-Jorgensen catalyst as an efficient and recyclable organocatalyst for asymmetric Michael addition reactions
Szczesniak, Piotr
Staszewska-Krajewska, Olga
Furman, Bartlomiej
Mlynarski, Jacek
TETRAHEDRON-ASYMMETRY, 2017, 28 (12) : 1765 - 1773
[42] Amino Imidate Catalyzed Asymmetric Michael Reactions of Ketones and Nitroalkenes
Sosunovych, Bohdan
Brown, Alexander J.
Clarke, Paul A.
SYNOPEN, 2022, 06 (01): : 67 - 74
[43] Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes
Polackova, Viera
Cmelova, Patricia
Gorova, Renata
Sebesta, Radovan
MONATSHEFTE FUR CHEMIE, 2018, 149 (04): : 729 - 736
[44] Efficient and Highly Enantioselective Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Surfactant-type Organocatalyst in the Presence of Water
Hu, Feng
Guo, Chang-Shan
Xie, Jin
Zhu, Hai-Liang
Huang, Zhi-Zhen
CHEMISTRY LETTERS, 2010, 39 (04) : 412 - 414
[45] Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes
Viera Poláčková
Patrícia Čmelová
Renáta Górová
Radovan Šebesta
Monatshefte für Chemie - Chemical Monthly, 2018, 149 : 729 - 736
[46] Asymmetric Michael addition reactions of aldehydes with nitrostyrenes catalyzed by functionalized chiral ionic liquids
Zhang, Qianying
Ni, Bukuo
Headley, Allan D.
TETRAHEDRON, 2008, 64 (22) : 5091 - 5097
[47] Asymmetric Organocatalytic Formal Aza-Michael Addition of Ammonia to Nitroalkenes
Lykke, Lennart
Monge, David
Nielsen, Martin
Jorgensen, Karl Anker
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (45) : 13330 - 13334
[48] Calcium-BINOL: a novel and efficient catalyst for asymmetric Michael reactions
Kumaraswamy, G
Sastry, MNV
Jena, N
TETRAHEDRON LETTERS, 2001, 42 (48) : 8515 - 8517
[49] A new polymer-anchored chiral catalyst for asymmetric Michael addition reactions
Sundararajan, G
Prabagaran, N
ORGANIC LETTERS, 2001, 3 (03) : 389 - 392
[50] A Nickel-Bisdiamine Porous Organic Polymer as Heterogeneous Chiral Catalyst for Asymmetric Michael Addition to Aliphatic Nitroalkenes
Buendia, Mikkel B.
Kegnaes, Soren
Kramer, Soren
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (23) : 5506 - 5512

← 1 2 3 4 5 →