N-Heterocyclic Carbene Catalyzed Cyclocondensation of α,β-Unsaturated Carboxylic Acids: Enantioselective Synthesis of Pyrrolidinone and Dihydropyridinone Derivatives

2014 ◽  
Vol 53 (43) ◽  
pp. 11611-11615 ◽  
Author(s):  
Xiang-Yu Chen ◽  
Zhong-Hua Gao ◽  
Chun-Yu Song ◽  
Chun-Lin Zhang ◽  
Zhi-Xiang Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Enantioselective Synthesis ◽  
Unsaturated Carboxylic Acids

N-Heterocyclic Carbene Catalyzed Cyclocondensation of α,β-Unsaturated Carboxylic Acids: Enantioselective Synthesis of Pyrrolidinone and Dihydropyridinone Derivatives

2014 ◽  
Vol 126 (43) ◽  
pp. 11795-11799 ◽  
Author(s):  
Xiang-Yu Chen ◽  
Zhong-Hua Gao ◽  
Chun-Yu Song ◽  
Chun-Lin Zhang ◽  
Zhi-Xiang Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Enantioselective Synthesis ◽  
Unsaturated Carboxylic Acids

N-Heterocyclic carbene-catalyzed [4 + 2] cyclization of α,β-unsaturated carboxylic acids bearing γ-H with isatins: an enantioselective synthesis of spirocyclic oxindole–dihydropyranones

2016 ◽  
Vol 14 (4) ◽  
pp. 1485-1491 ◽  
Author(s):  
Ling Zhu ◽  
Chenxia Yu ◽  
Tuanjie Li ◽  
Yuhong Wang ◽  
Yinan Lu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Enantioselective Synthesis ◽  
Unsaturated Carboxylic Acids ◽  
Spirocyclic Oxindole

An NHC-catalyzed asymmetric [4 + 2] annulation of isatins and α,β-unsaturated carboxylic acids bearing γ-H gave spirocyclic oxindole–dihydropyranones successfully via an in situ activation strategy.

An organocatalytic Michael-cyclization cascade of 4-oxa-α,β-unsaturated carboxylic acids with aldehydes: facile synthesis of chiral γ-lactols and trisubstituted γ-lactones

2015 ◽  
Vol 51 (17) ◽  
pp. 3596-3599 ◽  
Author(s):  
Jun-Bing Lin ◽  
Shi-Ming Xu ◽  
Ji-Kang Xie ◽  
Hong-Yu Li ◽  
Peng-Fei Xu
Keyword(s):  
Carboxylic Acids ◽  
Enantioselective Synthesis ◽  
Facile Synthesis ◽  
Unsaturated Carboxylic Acids

An organocatalytic Michael-cyclization cascade of 4-oxa-α,β-unsaturated carboxylic acids with aldehydes has been developed, enabling highly enantioselective synthesis of γ-lactols, trisubstituted γ-lactones and γ-lactams.

N-Heterocyclic carbene-catalyzed [4 + 2] annulation of α,β-unsaturated carboxylic acids: enantioselective synthesis of dihydropyridinones and spirocyclic oxindolodihydropyridinones

2016 ◽  
Vol 3 (1) ◽  
pp. 77-81 ◽  
Author(s):  
Wen-Qiang Jia ◽  
Han-Ming Zhang ◽  
Chun-Lin Zhang ◽  
Zhong-Hua Gao ◽  
Song Ye
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Enantioselective Synthesis ◽  
Unsaturated Carboxylic Acid ◽  
Unsaturated Carboxylic Acids

The N-heterocyclic carbene-catalyzed [4 + 2] annulation of α,β-unsaturated carboxylic acid with hydrazones and isatin-derived imines was developed, affording the corresponding dihydropyridinones, respectively, in good yields with high enantioselectivities.

Perturbation theory of substituent effect. Importance of the field effect in transmission of the substituent effect

1980 ◽  
Vol 45 (6) ◽  
pp. 1655-1661 ◽  
Author(s):  
Robert Ponec
Keyword(s):  
Perturbation Theory ◽  
Carboxylic Acids ◽  
Quantum Chemical ◽  
Substituent Effect ◽  
Field Effect ◽  
Adequate Description ◽  
Meta Position ◽  
Unsaturated Carboxylic Acids

Various quantum chemical approaches to the problem of transmission of the substituent effect were compared. It was shown that inclusion of the electronic repulsion (field effect) was necessary to give a true picture of differences in ρ constants for reactions of the cis and trans isomers of substituted unsaturated carboxylic acids; the same holds for an adequate description of transmission of the substituent effect from the meta position on a given skeleton.

scholarly journals A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

2020 ◽  
Vol 11 (21) ◽  
pp. 5572-5576 ◽  
Author(s):  
Noboru Hayama ◽  
Yusuke Kobayashi ◽  
Eriko Sekimoto ◽  
Anna Miyazaki ◽  
Kiyofumi Inamoto ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Michael Addition ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

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