Keto‐Enol Tautomerization Controls the Acid‐Catalyzed Robinson Annulation ‐ A DFT Study

2019 ◽  
Vol 4 (17) ◽  
pp. 4962-4966
Author(s):  
Shinichi Yamabe ◽  
Noriko Tsuchida ◽  
Shoko Yamazaki
Keyword(s):  
Dft Study ◽  
Acid Catalyzed ◽  
Robinson Annulation

Chiral Brønsted acid-catalyzed hydrophosphonylation of imines—DFT study on the effect of substituents of phosphoric acid

Tetrahedron ◽  
2009 ◽  
Vol 65 (26) ◽  
pp. 4950-4956 ◽  
Author(s):  
Takahiko Akiyama ◽  
Hisashi Morita ◽  
Prabhakar Bachu ◽  
Keiji Mori ◽  
Masahiro Yamanaka ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Dft Study ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Effect Of Substituents ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

Role of keto–enol tautomerization in a chiral phosphoric acid catalyzed asymmetric thiocarboxylysis of meso-epoxide: a DFT study

2015 ◽  
Vol 13 (45) ◽  
pp. 10981-10985 ◽  
Author(s):  
Manjaly J. Ajitha ◽  
Kuo-Wei Huang
Keyword(s):  
Density Functional Theory ◽  
Phosphoric Acid ◽  
Dft Calculations ◽  
Density Functional ◽  
Dft Study ◽  
Functional Theory ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

The mechanism of a chiral phosphoric acid catalyzed thiocarboxylysis of meso-epoxide was investigated by density functional theory (DFT) calculations (M06-2X).

DFT Study of the Isomerization of Hexyl Species Involved in the Acid-Catalyzed Conversion of 2-Methyl-Pentene-2

1999 ◽  
Vol 181 (1) ◽  
pp. 124-144 ◽  
Author(s):  
M.A. Natal-Santiago ◽  
R. Alcalá ◽  
J.A. Dumesic
Keyword(s):  
Dft Study ◽  
Acid Catalyzed

Mechanistic insight into the acid-catalyzed isomerization of biomass-derived polysubstituted pyrrolidines: an experimental and DFT study

2017 ◽  
Vol 15 (2) ◽  
pp. 426-434 ◽  
Author(s):  
Gabriela G. Gerosa ◽  
Nicolás Grimblat ◽  
Rolando A. Spanevello ◽  
Alejandra G. Suárez ◽  
Ariel M. Sarotti
Keyword(s):  
Dft Study ◽  
Computational Studies ◽  
Mechanistic Insight ◽  
Acid Catalyzed ◽  
Insight Into

The mechanism of the acid-catalyzed isomerization of polysubstituted pyrrolidines was unravelled by a combination of experimental, spectroscopic and computational studies.

scholarly journals Acid-Catalyzed Z-E Isomerization of γ-Alkylidenebutenolides: An Experimental and DFT Study

2020 ◽  
Author(s):  
Jodieh Varejão ◽  
Luiz Barbosa ◽  
Eduardo Varejão ◽  
Aline Souza ◽  
Mateus Lage ◽  
...  
Keyword(s):  
Dft Study ◽  
Acid Catalyzed

scholarly journals Comparative DFT study of metal-free Lewis acid-catalyzed C–H and N–H silylation of (hetero)arenes: mechanistic studies and expansion of catalyst and substrate scope

RSC Advances ◽  
2019 ◽  
Vol 9 (64) ◽  
pp. 37675-37685
Author(s):  
Pan Du ◽  
Jiyang Zhao
Keyword(s):  
Lewis Acid ◽  
Dft Study ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Acid Catalyzed

We investigated the mechanism of the dehydrosilylation of (hetero)arenes and extended the scope of the silylation catalysts and substrates.

The chemistry of thujone. XVII. The synthesis of ambergris fragrances and related analogues

1994 ◽  
Vol 72 (6) ◽  
pp. 1570-1581 ◽  
Author(s):  
James P. Kutney ◽  
Yong-Huang Chen
Keyword(s):  
Ring Opening ◽  
Sodium Acetate ◽  
Ring Closure ◽  
Side Chain ◽  
Synthetic Route ◽  
Acid Catalyzed ◽  
Robinson Annulation

A strategy to utilize the thujone-derived enone 1 for the development of a synthetic route to ambergris fragrances is presented. Thujone (8) is transformed to the tricyclic enone 9, via the Robinson annulation reaction, and the latter is then elaborated to the cis-fused tricyclic intermediates 10, 11, and 12. Extrusion of the isopropyl side chain in 12 is achieved through an initial ozonation reaction and the resulting ketone 14 is then treated with m-CPBA to afford 16. Cyclopropyl ring opening in 16 is performed via initial saponification to the alcohol 17 and the latter is then reacted with FeCl3 and sodium acetate to enone 1. The necessary elaboration of a tetrahydrofuran ring attached to ring B of 1 is achieved through reaction of 1 with vinylmagnesium bromide, alkylation, hydroboration, and final acid-catalyzed ring closure of the 1,5-diol 4. The route affords the opportunity of synthesizing a variety of analogues within the Ambrox series.

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