Brønsted acid catalyzed enantioselective inter and intramolecular α-amidoalkylation reactions in the synthesis of isoquinoline derivatives

2016 ◽  
Author(s):  
Eider Aranzamendi Uruburu ◽  
Nuria Sotomayor ◽  
Esther Lete
Keyword(s):  
Acid Catalyzed ◽  
Isoquinoline Derivatives

Intramolecular N-Acyliminium Ion-Olefin Cyclization in the Synthesis of Optically Pure Isoquinoline Derivatives: Control of Stereochemistry and Application to Synthesis of Morphine Alkaloids

1999 ◽  
Vol 64 (2) ◽  
pp. 203-216 ◽  
Author(s):  
Patricia Bottari ◽  
Mary Ann A. Endoma ◽  
Tomáš Hudlický ◽  
Ion Ghiviriga ◽  
Khalil A. Abboud
Keyword(s):  
Cyclization Reactions ◽  
Neighboring Group ◽  
Group Participation ◽  
Hydride Reduction ◽  
Morphine Alkaloids ◽  
Acid Catalyzed ◽  
Neighboring Group Participation ◽  
Isoquinoline Derivatives ◽  
Optically Pure

The 3-[2-(cyclohex-1-eneyl)ethyl]-[1,3]oxazoline-2,4-dione derivatives 9, 14 and 16 were subjected to hydride reduction followed by acid-catalyzed olefin-N-acyliminium ion cyclization to afford a series of perhydroisoquinolines 10, 11a, 11b, 19a-19c, 20a, 20b and 21. A mechanism was proposed that accounts for the observed stereoselectivity of the cyclization reactions based on the neighboring group participation by a benzoate group.

Synthesis of Indolo[1,2-b ]isoquinoline Derivatives by Lewis Acid-Catalyzed Intramolecular Friedel-Crafts Alkylation Reaction

2018 ◽  
Vol 2018 (22) ◽  
pp. 2817-2821 ◽  
Author(s):  
Jitendra Gour ◽  
Srikanth Gatadi ◽  
Atulya Nagarsenkar ◽  
Bathini Nagendra Babu ◽  
Y. V. Madhavi ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Alkylation Reaction ◽  
Acid Catalyzed ◽  
Isoquinoline Derivatives

Acid Catalyzed Furan Ring Transposition

10.1039/sp768 ◽  
2014 ◽  
Author(s):  
Jamsheena V. ◽  
Ravindra Phatake
Keyword(s):  
Furan Ring ◽  
Acid Catalyzed

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes

2019 ◽  
Author(s):  
Juha Siitonen ◽  
Padmanabha V. Kattamuri ◽  
Muhammed Yousufuddin ◽  
Laszlo Kurti
Keyword(s):  
Total Synthesis ◽  
Acid Catalysts ◽  
Mechanistic Studies ◽  
Arylboronic Acid ◽  
Synthetic Utility ◽  
Acid Catalyzed

Unprotected keto- and aldoximes are readily <i>C</i>-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted <i>N</i>-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid <i>N</i>-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.<br>

Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Acid Catalyzed ◽  
Reaction Media ◽  
Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

Ascorbic acid-Catalyzed One-Pot Three-Component Biginelli Reaction: A Practical and Green Approach towards Synthesis of 3,4-dihydropyrimidin- 2(1H)-ones/thiones

2013 ◽  
Vol 10 (7) ◽  
pp. 463-467 ◽  
Author(s):  
Imene Sehout ◽  
Raouf Boulcina ◽  
Boudjemaa Boumoud ◽  
Fabienne Berree ◽  
Bertrand Carboni ◽  
...  
Keyword(s):  
Ascorbic Acid ◽  
Biginelli Reaction ◽  
One Pot ◽  
Green Approach ◽  
Acid Catalyzed
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