Synthesis applications of cationic aza-Cope rearrangements. Part 18. Scope and mechanism of tandem cationic aza-Cope rearrangement-Mannich cyclization reactions

1988 ◽  
Vol 110 (13) ◽  
pp. 4329-4336 ◽  
Author(s):  
E. Jon. Jacobsen ◽  
Jeremy. Levin ◽  
Larry E. Overman
Keyword(s):  
Cope Rearrangement ◽  
Cyclization Reactions ◽  
Mannich Cyclization ◽  
Cope Rearrangements

Aromatic Cope Rearrangements

2021 ◽  
Author(s):  
Breanna Tomiczek ◽  
Alexander Grenning
Keyword(s):  
Cope Rearrangement ◽  
Aromatic System ◽  
Cope Rearrangements

Reviewed herein is the aromatic Cope rearrangement, a Cope rearrangement where one (or both) of the alkenes of the 1,5-diene are part of a greater aromatic system. While the Cope...

ChemInform Abstract: Quinine-Catalyzed Asymmetric Domino Mannich-Cyclization Reactions of 3-Isothiocyanato Oxindoles with Imines for the Synthesis of Spirocyclic Oxindoles.

ChemInform ◽  
2015 ◽  
Vol 46 (24) ◽  
pp. no-no
Author(s):  
Mei Bai ◽  
Bao-Dong Cui ◽  
Jian Zuo ◽  
Jian-Qiang Zhao ◽  
Yong You ◽  
...  
Keyword(s):  
Cyclization Reactions ◽  
Mannich Cyclization

A Caveat Concerning Anionic Oxy-cope Rearrangements Within Bicyclo[2.2.2]octenyl Frameworks

1996 ◽  
Vol 49 (5) ◽  
pp. 639 ◽  
Author(s):  
MG Banwell ◽  
JR Dupuche ◽  
RW Gable
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Cope Rearrangement ◽  
Diels Alder Reaction ◽  
Cope Rearrangements ◽  
Potassium Hydride

Compounds (10), (15) and (16) all react with potassium hydride at 0°C to give, via retro- Diels-Alder reaction, 1-methylnaphthalene (12) in 60-67% yield. No evidence could be obtained for the formation of a product derived from the anionic oxy-Cope rearrangement of substrate (16).

Part 2: Efficient strategies for the construction of variably substituted bicyclo[5.3.1]undecenones (AB-taxane ring systems) and their conversion to tricyclo[9.3.1.03,8]pentadecenones (ABC taxane ring systems) and bicyclo[2.2.2]octanones

2004 ◽  
Vol 82 (2) ◽  
pp. 227-239 ◽  
Author(s):  
Nidia P Villalva-Servín ◽  
Alain Laurent ◽  
Alex G Fallis
Keyword(s):  
Lewis Acid ◽  
Sigmatropic Rearrangement ◽  
Diels Alder ◽  
Direct Access ◽  
Cope Rearrangement ◽  
Ring Closing Metathesis ◽  
Ring Systems ◽  
Sigmatropic Rearrangements ◽  
Key Words Magnesium ◽  
Cope Rearrangements

The extension of our strategies for the construction of cyclic molecules containing variably substituted bicyclo[5.3.1]undecenones (AB taxane ring systems) for the synthesis of the tricyclo[9.3.1.03,8]pentadecenone (ABC taxane ring system) and bicyclo[2.2.2]octanones are described. These routes employ a multi-component coupling protocol that employs sequential magnesium-mediated carbometallation of allyl-substituted propargyl alcohols followed by diastereoselective Lewis acid catalyzed intramolecular Diels–Alder reactions (IMDA). Subsequent ring-closing metathesis (RCM) afforded the ABC taxane core structure. Enone accelerated [3,3] sigmatropic rearrangements (Cope rearrangements) generated the bicyclo[2.2.2]octanone nucleus. In the presence of a Lewis acid, the dienophile precursor underwent a tandem reaction via the adduct directly to the bicyclo[2.2.2]octanones. This is the first example of a novel enone accelerated carbocycle Cope rearrangement and provides direct access to bicyclo[2.2.2]octanones by a new route that compliments the traditional cyclohexadiene cycloaddition approach. Key words: magnesium chelate, Lewis acid, taxanes, Diels–Alder, sigmatropic rearrangement, oxy-Cope, ring-closing metathesis, bicyclo[2.2.2]octanone.

Controlling Diastereoselectivity in the Tandem Microwave-Assisted Aza-Cope Rearrangement—Mannich Cyclization.

ChemInform ◽  
2007 ◽  
Vol 38 (32) ◽  
Author(s):  
Benjamin F. Johnson ◽  
Edwin L. Marrero ◽  
Wesley A. Turley ◽  
Harriet A. Lindsay
Keyword(s):  
Cope Rearrangement ◽  
Microwave Assisted ◽  
Mannich Cyclization
Sign in / Sign up

Export Citation Format

Share Document