Enantioselective Total Syntheses of Lyconadins A–E through a Palladium‐Catalyzed Heck‐Type Reaction

2020 ◽  
Vol 132 (7) ◽  
pp. 2882-2888 ◽  
Author(s):  
Jiayang Zhang ◽  
Yangtian Yan ◽  
Rong Hu ◽  
Ting Li ◽  
Wen‐Ju Bai ◽  
...  
Keyword(s):  
Total Syntheses ◽  
Type Reaction ◽  
Palladium Catalyzed

Enantioselective Total Syntheses of Lyconadins A–E through a Palladium‐Catalyzed Heck‐Type Reaction

2020 ◽  
Vol 59 (7) ◽  
pp. 2860-2866 ◽  
Author(s):  
Jiayang Zhang ◽  
Yangtian Yan ◽  
Rong Hu ◽  
Ting Li ◽  
Wen‐Ju Bai ◽  
...  
Keyword(s):  
Total Syntheses ◽  
Type Reaction ◽  
Palladium Catalyzed

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

Synthesis ◽  
2020 ◽  
Author(s):  
Lili Shi ◽  
Junkai Fu ◽  
Shuangqiu Gao ◽  
Le Chang ◽  
Binglin Wang
Keyword(s):  
Heck Reaction ◽  
Alkyl Radicals ◽  
Type Reaction ◽  
The Past ◽  
Alkyl Electrophiles ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Initial Work ◽  
Activated Olefins ◽  
Pseudo Halides

AbstractThe Mizoroki–Heck reaction is considered as one of the most ingenious and widely used methods for constructing C–C bonds. This reaction mainly focuses on activated olefins (styrenes, acrylates, or vinyl ethers) and aryl/vinyl (pseudo) halides. In comparison, the studies on unactivated alkenes and alkyl electrophiles are far less due to the low reactivity, poor selectivity, as well as competitive β-H elimination. In the past years, a growing interest has thus been devoted and significant breakthroughs have been achieved in the employment of unactivated alkenes and alkyl electrophiles as the reaction components, and this type of coupling is called as Heck-type or Heck-like reaction, which distinguishes from the traditional Heck reaction. Herein, we give a brief summary on Heck-type reaction between unactivated alkenes and alkyl electrophlies, covering its initial work, recent advancements, and mechanistic discussions.1 Introduction2 Intramolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles2.1 Cobalt-Catalyzed Intramolecular Heck-Type Reaction2.2 Palladium-Catalyzed Intramolecular Heck-Type Reaction2.3 Nickel-Catalyzed Intramolecular Heck-Type Reaction2.4 Photocatalysis and Multimetallic Protocol for Intramolecular Heck-Type Reaction3 Intermolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles3.1 Electrophilic Trifluoromethylating Reagent as Reaction Partners3.2 Alkyl Electrophiles as Reaction Partners4 Oxidative Heck-Type Reaction of Unactivated Alkenes and Alkyl Radicals5 Conclusions and Outlook

scholarly journals Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles

RSC Advances ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 909-917
Author(s):  
Antonio Arcadi ◽  
Giancarlo Fabrizi ◽  
Andrea Fochetti ◽  
Francesca Ghirga ◽  
Antonella Goggiamani ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Type Reaction ◽  
Palladium Catalyzed

The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles.

Total Syntheses of Enokipodins A and B Utilizing Palladium-Catalyzed Addition of An Arylboronic Acid to An Allene

2009 ◽  
Vol 11 (6) ◽  
pp. 1441-1443 ◽  
Author(s):  
Masahiro Yoshida ◽  
Yasunobu Shoji ◽  
Kozo Shishido
Keyword(s):  
Arylboronic Acid ◽  
Total Syntheses ◽  
Palladium Catalyzed

Total Syntheses of Prothracarcin and Tomaymycin by Use of Palladium Catalyzed Carbonylation

Tetrahedron ◽  
1986 ◽  
Vol 42 (14) ◽  
pp. 3793-3806 ◽  
Author(s):  
Miwako Mori ◽  
Yasuhiro Uozumi ◽  
Masaya Kimura ◽  
Yoshio Ban
Keyword(s):  
Total Syntheses ◽  
Palladium Catalyzed

A General Synthesis of Fluoroalkylated Alkenes by Palladium-Catalyzed Heck-Type Reaction of Fluoroalkyl Bromides

2014 ◽  
Vol 127 (4) ◽  
pp. 1286-1290 ◽  
Author(s):  
Zhang Feng ◽  
Qiao-Qiao Min ◽  
Hai-Yang Zhao ◽  
Ji-Wei Gu ◽  
Xingang Zhang
Keyword(s):  
Type Reaction ◽  
Palladium Catalyzed ◽  
General Synthesis
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