Water-assisted isomerization of the [H, C, N, O] system

Cao, Jun; Wang, Zhi Xiang; Gao, Lou Jun; Feng, Feng

doi:10.1007/s00894-015-2628-y

Cited by 5 publications

(3 citation statements)

References 29 publications

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“…It is also reasonable to rationalise the formation of 10a along this pathway. The validity of this and closely related reaction pathways is further supported by other well-documented examples [31,32].…”

Section: Synthesis Of Aminodiols Via Reductive Amination Of Perillald...supporting

confidence: 68%

Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers

Háznagy,

Csámpai,

Ugrai

et al. 2024

IJMS

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A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (−)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO4/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (−)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO4/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the N-benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ee), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues.

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Section: Synthesis Of Aminodiols Via Reductive Amination Of Perillald...supporting

confidence: 68%

Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers

Háznagy,

Csámpai,

Ugrai

et al. 2024

IJMS

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“…Formation of isomers of HNCO could potentially enhance oxidation, similarly to what is observed for HCN (see section 3.4). The isomerization pathways for HNCO have been studied theoretically by several groups [108,179,180] who nd the pathway to HOCN to be energetically the most favorable. However, the overall barrier height is of the order of 90 kcal mol −1 , which is too high for the process to be signicant at the present temperatures.…”

Section: Modeling Hnco Oxidationmentioning

confidence: 99%

Modeling nitrogen chemistry in combustion

Glarborg

Miller

Ruščić

et al. 2018

Progress in Energy and Combustion Science

1,314

748

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“…Precisely, isomerism and rich potential energy surfaces are unrivaled characteristics of the biogenic [H, C, N, O] system − that provides an ideal candidate to evaluate the quality of PESs derived from different methods. Indeed, this is one of the most important and oldest systems related to PES investigation .…”

Section: Introductionmentioning

confidence: 99%

Artificial Neural Network-Derived Unified Six-Dimensional Potential Energy Surface for Tetra Atomic Isomers of the Biogenic [H, C, N, O] System

Arab

Nazari

Illas

2023

J. Chem. Theory Comput.

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Recognition of different structural patterns in different potential energy surface regions, such as in isomerizing quasilinear tetra atomic molecules, is important for understanding the details of underlying physics and chemistry. In this respect, using three variants of artificial neural networks (ANNs), we investigated the six-dimensional (6-D) singlet potential energy surfaces (PES) of tetra atomic isomers of the biogenic [H, C, N, O] system. At first, we constructed a separate ANN potential for each of the studied isomers. In the next step, a comparative assessment of the separate ANN models led to the setting up of a unified 6-D singlet PES equally and accurately describing all studied isomers. The constructed unified model yields relative energies comparable to those obtained either from the gold standard CCSD(T) method or from separate ANNs for each of the studied isomers. The accuracy of the unified singlet PES is on the order of 10 −4 Hartrees (0.1 kcal/mol). The developed PES in this work captures the main features of nonlinear and quasilinear tetra atomic isomers of this biogenic system.

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Water-assisted isomerization of the [H, C, N, O] system

Cited by 5 publications

References 29 publications

Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers

Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers

Modeling nitrogen chemistry in combustion

Artificial Neural Network-Derived Unified Six-Dimensional Potential Energy Surface for Tetra Atomic Isomers of the Biogenic [H, C, N, O] System

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