scholarly journals Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study

Molecules ◽  
2020 ◽  
Vol 25 (20) ◽  
pp. 4811
Author(s):  
Marc Presset ◽  
Michel Rajzmann ◽  
Guillaume Dauvergne ◽  
Jean Rodriguez ◽  
Yoann Coquerel
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Theoretical Study ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dft Methods ◽  
Wolff Rearrangement ◽  
Functional Theory ◽  
Thermally Induced ◽  
Diels Alder Reaction

Inversions in the periselectivity of formal aza-Diels–Alder cycloadditions between α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was observed, too. These variations in selectivities were fully rationalized by computational modeling using density functional theory (DFT) methods.

Theoretical Study of the Diels-Alder Reaction in the Synthesis of Abietane Diterpenes

2014 ◽  
Vol 608-609 ◽  
pp. 981-984
Author(s):  
Rui Huan Du ◽  
Bai Qin Zheng ◽  
Jian Min Zhang
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Energy Surface ◽  
Theoretical Study ◽  
Alder Reaction ◽  
Diels Alder ◽  
Functional Theory ◽  
Diels Alder Reaction ◽  
Abietane Diterpenes ◽  
Ring Transition State

Density Functional Theory (DFT),at the B3LYP/6-311 G(d,p) level of theory and Moller-Plesse Theory (MP2/6-311G (d,p)) has been performed to study the mechanism, potential energy surface of the Diels-Alder reaction in the Synthesis of abietane diterpenes. The obtained results indicate that the reaction is concerted and synchronous processes. The transannular product is formed via a six-member ring transition state; yield of the endo product is higher. And finally, the enthalpie and activation energie of the reaction are given respectively. The reaction is exothermic,which accords well with experimental observation.

Reactivity descriptor for the retro Diels–Alder reaction of partially saturated 2-pyrones: DFT study on substituents and solvent effects

RSC Advances ◽  
2016 ◽  
Vol 6 (103) ◽  
pp. 101697-101706 ◽  
Author(s):  
Tuhin S. Khan ◽  
Shelaka Gupta ◽  
Md. Imteyaz Alam ◽  
M. Ali Haider
Keyword(s):  
Density Functional Theory ◽  
Dft Calculations ◽  
Density Functional ◽  
Alder Reaction ◽  
Diels Alder ◽  
Polar Solvents ◽  
Functional Theory ◽  
Partially Saturated ◽  
Diels Alder Reaction ◽  
Reactivity Descriptor

​The retro-Diels–Alder (rDA) reaction of partially saturated 2-pyrones were studied using density functional theory (DFT) calculations in polar and non-polar solvents, and fundamental descriptors were proposed to understand the electronic and solvent effect.

Multiple Activation Catalyst for Asymmetric [4+2] Cycloaddition of Aldehydes with Dienes

Synlett ◽  
2021 ◽  
Author(s):  
Takuya Kurahashi ◽  
Seijiro Matsubara ◽  
Rei Tomifuji ◽  
Shunpei Murano ◽  
Satoru Teranishi ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Addition Reaction ◽  
Catalyst System ◽  
Alder Reaction ◽  
Diels Alder ◽  
Functional Theory ◽  
Diels Alder Reaction ◽  
Chiral Phosphoric Acid ◽  
High Yields

AbstractThe enantioselective oxa-Diels–Alder reaction of nonactivated substrates by utilizing FeCl3 and a 1,1′-bi-2-naphthol (BINOL) derived chiral phosphoric acid as a multiple activation catalyst is reported. Various oxygen-containing six-membered heterocycles were obtained in high yields and in an enantioselective manner. Density functional theory (DFT) calculations elucidate that both Lewis acidic and Brønsted acidic moieties in the catalyst system synergistically activate two lone pairs of an aldehyde to facilitate enantioselective addition reaction of dienes.

scholarly journals Electron Dynamics with Explicit-Time Density Functional Theory of the [4+2] Diels–Alder Reaction

2020 ◽  
Vol 16 (4) ◽  
pp. 2172-2180
Author(s):  
Angela Acocella ◽  
Tainah D. Marforio ◽  
Matteo Calvaresi ◽  
Andrea Bottoni ◽  
Francesco Zerbetto
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Alder Reaction ◽  
Diels Alder ◽  
Electron Dynamics ◽  
Functional Theory ◽  
Diels Alder Reaction ◽  
Time Density
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