Enantioselective Diels-Alder Cycloadditions with β-Substituted Pyrazolidinone Propiolimides

被引：6

作者：

Sibi, Mukund P. ^{[1
]}

Cruz, Wilfredo, Jr. ^{[1
]}

Stanley, Levi M. ^{[1
]}

机构：

[1] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA

来源：

SYNLETT | 2010年 / 06期

关键词：

Diels-Alder cycloaddition; acetylenic dienophile; enantioselective; pyrazolidinone; chiral Lewis acid; LEWIS-ACID CATALYSTS; CHIRAL RELAY; LIGANDS; CYCLOPENTADIENE; TEMPLATES; OLEFINS; EXO;

D O I：

10.1055/s-0029-1219538

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral Lewis acid catalyzed Diels-Alder cycloadditions between beta-substituted pyrazolidinone propiolimides and cyclic dienes have been studied. A catalyst prepared from Sc(OTf)(3) and t-Bu-pybox ligand promotes the formation of enantioenriched diene cycloadducts in moderate to high yield and good enantioselectivity from the reactions of acetylenic dienophiles and cyclic dienes.

引用

页码：889 / 892

页数：4

共 50 条

[31] Conformationally flexible chiral supramolecular catalysts for enantioselective Diels-Alder reactions with anomalous endo/exo selectivities
Hatano, Manabu
Ishihara, Kazuaki
CHEMICAL COMMUNICATIONS, 2012, 48 (36) : 4273 - 4283
[32] Strategies for remote enantiocontrol in chiral gold(iii) complexes applied to catalytic enantioselective γ,δ-Diels-Alder reactions
Reid, Jolene P.
Hu, Mingyou
Ito, Susumu
Huang, Banruo
Hong, Cynthia M.
Xiang, Hengye
Sigman, Matthew S.
Toste, F. Dean
CHEMICAL SCIENCE, 2020, 11 (25) : 6450 - 6456
[33] A deconjugative alkylation/Diels-Alder cycloaddition strategy to synthesize 2-substituted bicyclic scaffolds
Zhang, Wei
Ghiviriga, Ion
Grenning, Alexander J.
TETRAHEDRON, 2017, 73 (29) : 4076 - 4083
[34] STEREOSELECTIVE SYNTHESIS OF NOVEL DIELS-ALDER ADDUCTS OF p-SUBSTITUTED METHYL THIOCINNAMATES AND CYCLOPENTADIENE
Camilo, Fernanda F.
Gruber, Jonas
SYNTHETIC COMMUNICATIONS, 2012, 42 (03) : 394 - 401
[35] Gold(I)-Initiated Cycloisomerization/Diels-Alder/Retro-Diels-Alder Cascade Strategy to Biaryls
Jin, Shengfei
Niu, Yujie
Liu, Chengjun
Zhu, Lifeng
Li, Yangming
Cui, Shanshan
Xiong, Zhiling
Cheng, Maosheng
Lin, Bin
Liu, Yongxiang
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17) : 9066 - 9074
[36] Diels-Alder trapping vs. amidoalkylation of cyclopentadiene with polychloroacetaldehyde sulfonylimines
Chernysheva, Gulnur N.
Katerinich, Maxim D.
Ushakov, Igor A.
Rozentsveig, Igor B.
MENDELEEV COMMUNICATIONS, 2020, 30 (05) : 618 - 620
[37] The Role of Supramolecular Intermediates in the Potential Energy Surface of the Diels-Alder Reaction
Ramirez-Gualito, Karla
Lopez-Mora, Nestor
Jimenez-Vazquez, Hugo A.
Tamariz, Joaquin
Cuevas, Gabriel
JOURNAL OF THE MEXICAN CHEMICAL SOCIETY, 2013, 57 (04) : 267 - 275
[38] Catalytic Enantioselective Inverse-Electron-Demand Diels-Alder Reaction of 2-Pyrones and Vinyl Selenides
You, Xin-Yu
Cai, Quan
SYNLETT, 2023, 34 (08) : 948 - 952
[39] Enantioselective Diels-Alder Reactions of Carboxylic Ester Dienophiles Catalysed by Titanium-Based Chiral Lewis Acid
Choughule, Yogesh K.
Patwardhan, Anand V.
ORIENTAL JOURNAL OF CHEMISTRY, 2016, 32 (02) : 921 - 926
[40] L-Pyroglutamic Sulphonamide as Hydrogen-Bonding Organocatalyst: Enantioselective Diels-Alder Cyclization to Construct Carbazolespirooxindoles
Ren, Ji-Wei
Wang, Jing
Xiao, Jun-An
Li, Jun
Xiang, Hao-Yue
Chen, Xiao-Qing
Yang, Hua
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (12) : 6441 - 6449

← 1 2 3 4 5 →