Transition-Metal-Mediated Cascade Reactions:  The Water-Accelerated Carboalumination−Claisen Rearrangement−Carbonyl Addition Reaction

2005 ◽  
Vol 70 (20) ◽  
pp. 8096-8102 ◽  
Author(s):  
Peter Wipf ◽  
David L. Waller ◽  
Jonathan T. Reeves
Keyword(s):  
Transition Metal ◽  
Claisen Rearrangement ◽  
Addition Reaction ◽  
Cascade Reactions ◽  
Carbonyl Addition

Transition Metal-Free Cascade Reactions of Alkynols to Afford Isoquinolin-1(2H)-one and Dihydroisobenzofuran Derivatives

2014 ◽  
Vol 79 (10) ◽  
pp. 4602-4614 ◽  
Author(s):  
Deng Yuan Li ◽  
Ke Ji Shi ◽  
Xiao Feng Mao ◽  
Guo Rong Chen ◽  
Pei Nian Liu
Keyword(s):  
Transition Metal ◽  
Cascade Reactions ◽  
Metal Free

Toward the total synthesis of lophotoxin — New methodologies and synthetic strategies

2006 ◽  
Vol 84 (10) ◽  
pp. 1226-1241 ◽  
Author(s):  
Peter Wipf ◽  
Michel Grenon
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Recent Progress ◽  
Furan Ring ◽  
Addition Reaction ◽  
Thermal Conditions ◽  
Preliminary Results ◽  
Keto Esters ◽  
New Methodologies ◽  
Metal Catalyzed

Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal-catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring formation either under thermal conditions or by microwave irradiation.Key words: 1,6-addition, organocuprates, catalytic desymmetrization, furan cyclization, microwave.

A Concise Total Synthesis of (±)-Mesembrine

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1203-1206 ◽  
Author(s):  
Hyoungsu Kim ◽  
Hosam Choi ◽  
Kiyoun Lee
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Allylic Oxidation ◽  
Quaternary Stereocenter

A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson–Claisen rearrangement for the formation of the benzylic quaternary stereocenter and direct allylic oxidation to generate the substrate for the amidation/transannular aza-conjugate addition reaction.

Preparation of pyridine nucleotide analogs by the carbonyl addition reaction

1957 ◽  
Vol 70 (1) ◽  
pp. 87-106 ◽  
Author(s):  
Robert Main Burton ◽  
Anthony San Pietro ◽  
Nathan O. Kaplan
Keyword(s):  
Addition Reaction ◽  
Pyridine Nucleotide ◽  
Nucleotide Analogs ◽  
Carbonyl Addition

Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from gem-difluorochloro ethanes

2019 ◽  
Vol 55 (95) ◽  
pp. 14355-14358
Author(s):  
Shyamsundar Das ◽  
Nakeun Ko ◽  
Eunsung Lee ◽  
Sang Eun Kim ◽  
Byung Chul Lee
Keyword(s):  
Transition Metal ◽  
Claisen Rearrangement ◽  
Cascade Reaction ◽  
One Pot ◽  
Metal Free

Herein, we describe a new transition metal-free Claisen rearrangement for the synthesis of α-substituted 2,4-dienamide. This one-pot, stereoselective three-component cascade reaction affords various polysubstituted 2,4-dienamides in good yields.

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