Recent developments in asymmetric Heck type cyclization reactions for constructions of complex molecules

2021 ◽  
Author(s):  
Alexander N. Reznikov ◽  
Maria A. Ashatkina ◽  
Yuri N. Klimochkin
Keyword(s):  
Heck Reaction ◽  
Cyclization Reactions ◽  
Complex Molecules ◽  
Recent Developments ◽  
Intramolecular Heck Reaction ◽  
Literature Coverage

This review summarizes the recent developments in the asymmetric intramolecular Heck reaction and carbometallation-initiated cascade transformations including Ni-catalyzed processes with literature coverage mainly extending from 2016 to 2021.

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 Activation modes in biocatalytic radical cyclization reactions

2021 ◽  
Author(s):  
Yuxuan Ye ◽  
Haigen Fu ◽  
Todd K Hyster
Keyword(s):  
Heme Iron ◽  
Radical Cyclization ◽  
Cytochrome P450 Monooxygenases ◽  
Radical Cyclizations ◽  
Cyclization Reactions ◽  
Complex Molecules ◽  
P450 Monooxygenases ◽  
Non Heme Iron ◽  
Essential Reactions ◽  
Isopenicillin N

Abstract Radical cyclizations are essential reactions in the biosynthesis of secondary metabolites and the chemical synthesis of societally valuable molecules. In this review, we highlight the general mechanisms utilized in biocatalytic radical cyclizations. We specifically highlight cytochrome P450 monooxygenases (P450s) involved in the biosynthesis of mycocyclosin and vancomycin, non-heme iron- and α-ketoglutarate-dependent dioxygenases (Fe/αKGDs) used in the biosynthesis of kainic acid, scopolamine, and isopenicillin N, and radical S-adenosylmethionine (SAM) enzymes that facilitate the biosynthesis of oxetanocin A, menaquinone, and F420. Beyond natural mechanisms, we also examine repurposed flavin-dependent ‘ene’-reductases (ERED) for non-natural radical cyclization. Overall, these general mechanisms underscore the opportunity for enzymes to augment and enhance the synthesis of complex molecules using radical mechanisms.

scholarly journals Approaches to the Cephalotaxine Skeleton Using an Intramolecular Heck Reaction.

1998 ◽  
Vol 46 (7) ◽  
pp. 1084-1089 ◽  
Author(s):  
Masazumi IKEDA ◽  
Ken-ichi HIROSE ◽  
Serry A.A. EL BIALY ◽  
Tatsunori SATO ◽  
Takayuki YAKURA ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Intramolecular Heck Reaction

First total synthesis of antihypertensive natural products S-(+)-XJP and R-(−)-XJP

2014 ◽  
Vol 12 (37) ◽  
pp. 7338-7344 ◽  
Author(s):  
Chaolei Wang ◽  
Guoxiang Wei ◽  
Xue Yang ◽  
Hequan Yao ◽  
Jieyun Jiang ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Heck Reaction ◽  
Intramolecular Heck Reaction

The first total synthesis of S-(+)-XJP and R-(−)-XJP has been achieved via intramolecular Heck reaction. A latent functionality strategy was implemented to circumvent the racemization in this endeavor.

scholarly journals Recent Developments in Polyene Cyclizations and Their Applications in Natural Product Synthesis

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 67-82 ◽  
Author(s):  
Anthony Barrett ◽  
Tsz-Kan Ma ◽  
Thomas Mies
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Lewis Acid ◽  
Multiple Bond ◽  
Natural Product Synthesis ◽  
Cyclization Reactions ◽  
Cascade Cyclizations ◽  
Highly Efficient ◽  
Recent Developments ◽  
Radical Cascade

Cascade polyene cyclization reactions are highly efficient and elegant bioinspired transformations that involve simultaneous multiple bond constructions to rapidly generate complex polycyclic molecules. This review summarizes the most prominent work on a variety of cationic and radical cascade cyclizations and their applications in natural product synthesis published between 2014 and 2018.1 Introduction2 Cationic Polyene Cyclizations2.1 Lewis Acid Mediated Polyene Cyclizations2.2 Brønsted Acid Mediated Polyene Cyclizations2.3 Halogen Electrophile Initiated Polyene Cyclizations2.4 Sulfur Electrophile Initiated Polyene Cyclizations2.5 Transition-Metal-Mediated Cationic Polyene Cyclizations3 Radical Polyene Cyclizations3.1 Transition-Metal-Mediated Radical Polyene Cyclizations3.2 Photocatalyst-Mediated Polyene Cyclizations4 Origin of Stereocontrol in Polyene Cyclizations5 Conclusion

scholarly journals Recent developments in cyclization reactions of α-aminoalkyl radicals

ARKIVOC ◽  
2004 ◽  
Vol 2004 (14) ◽  
pp. 10-35 ◽  
Author(s):  
José M. Aurrecoechea ◽  
Rubén Suero
Keyword(s):  
Cyclization Reactions ◽  
Recent Developments

ChemInform Abstract: New MCR Based on Intramolecular Heck Reaction under Aerobic Conditions: A Direct Access to Cytotoxic Fused N-Heterocycles.

ChemInform ◽  
2015 ◽  
Vol 46 (15) ◽  
pp. no-no
Author(s):  
Raju Adepu ◽  
Bagineni Prasad ◽  
Mohd Ashraf Ashfaq ◽  
Nasreen Z. Ehtesham ◽  
Manojit Pal
Keyword(s):  
Heck Reaction ◽  
Direct Access ◽  
Aerobic Conditions ◽  
Intramolecular Heck Reaction
Sign in / Sign up

Export Citation Format

Share Document