ChemInform Abstract: Focused Update on the Prins Reaction and the Prins Cyclization

ChemInform ◽  
2012 ◽  
Vol 43 (38) ◽  
pp. no-no
Author(s):  
Isidro M. Pastor ◽  
Miguel Yus
Keyword(s):  
Prins Reaction ◽  
Prins Cyclization

Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D

2014 ◽  
Vol 12 (36) ◽  
pp. 7026-7035 ◽  
Author(s):  
Anil K. Saikia ◽  
Kiran Indukuri ◽  
Jagadish Das
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Acyliminium Ions

A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications

Synthesis ◽  
2020 ◽  
Vol 52 (14) ◽  
pp. 1991-2007 ◽  
Author(s):  
Alison J. Frontier ◽  
Shukree Abdul-Rashed ◽  
Connor Holt
Keyword(s):  
Natural Products ◽  
Small Molecules ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Pericyclic Reactions ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Synthetic Utility ◽  
Cascade Processes ◽  
Saturated Heterocycles

This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization­ processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing­ saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericyclic reactions, including [4+2] cycloadditions and Nazarov electrocyclizations, to rapidly construct complex small molecules. Finally, examples of the use of alkynyl Prins and alkynyl aza-Prins reactions in the synthesis of natural products are described. The review covers the literature through the end of 2019.1 Introduction1.1 Alkyne-Carbonyl Coupling Pathways1.2 Coupling/Cyclization Cascades Using the Alkynyl Prins Reaction2 Alkynyl Prins Annulation (Oxocarbenium Electrophiles)2.1 Early Work2.2 Halide as Terminal Nucleophile2.3 Oxygen as Terminal Nucleophile2.4 Arene as Terminal Nucleophile (Intermolecular)2.5 Arene Terminal Nucleophile (Intramolecular)2.6 Cyclizations Terminated by Elimination3 Synthetic Utility of Alkynyl Prins Annulation3.1 Alkynyl Prins-Mediated Synthesis of Dienes for a [4+2] Cyclo­- addition­-Oxidation Sequence3.2 Alkynyl Prins Cyclization Adducts as Nazarov Cyclization Precursors3.3 Alkynyl Prins Cyclization in Natural Product Synthesis4 Alkynyl Aza-Prins Annulation4.1 Iminium Electrophiles4.2 Activated Iminium Electrophiles5 Alkynyl Aza-Prins Cyclizations in Natural Product Synthesis6 Summary and Outlook

scholarly journals Synthesis of Nitrogen- and Oxygen-Containing Heterocycles by Prins Cyclization in Continuous Flow

Synthesis ◽  
2020 ◽  
Author(s):  
Armando Talavera-Alemán ◽  
Guillaume Dagousset ◽  
Christine Thomassigny ◽  
Jérome Marrot
Keyword(s):  
Continuous Flow ◽  
Flow Chemistry ◽  
Prins Reaction ◽  
Cyclization Reactions ◽  
Prins Cyclization ◽  
Anti Isomer ◽  
Bicyclic Compounds ◽  
Continuous Flow Chemistry

AbstractAza-silyl-Prins and oxa-Prins cyclization reactions in continuous-flow chemistry are described for the synthesis of the corresponding tetrahydropyridines and pyran derivatives, respectively. In particular, the use of pyridine-carboxaldehydes for aza-silyl-Prins reaction led to either a symmetrical triarylmethane or two new bicyclic compounds. 4-Fluorinated-2-substituted tetrahydropyran derivatives were also obtained in the oxa-Prins cyclization with good selectivity in favor of the anti-isomer.

Prins cyclization of α-bromoethers under basic conditions

2013 ◽  
Vol 91 (12) ◽  
pp. 1193-1201 ◽  
Author(s):  
Patrice Arpin ◽  
Bryan Hill ◽  
Robin Larouche-Gauthier ◽  
Claude Spino
Keyword(s):  
Lewis Acid ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Acid Catalyzed ◽  
Markovnikov Addition

α-Bromoethers have been found to undergo Prins-type cyclization under basic conditions and without the need to add a promoter. The products are those derived from a Markovnikov addition on the pendant alkene. However, the stereochemistry and even the structure of the products sometimes differ from those expected with the classical Lewis-acid-catalyzed Prins reaction of acetals.

Focused Update on the Prins Reaction and the Prins Cyclization

2012 ◽  
Vol 16 (10) ◽  
pp. 1277-1312 ◽  
Author(s):  
Isidro M. Pastor ◽  
Miguel Yus
Keyword(s):  
Prins Reaction ◽  
Prins Cyclization

scholarly journals Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

2021 ◽  
Vol 17 ◽  
pp. 932-963
Author(s):  
Asha Budakoti ◽  
Pradip Kumar Mondal ◽  
Prachi Verma ◽  
Jagadish Khamrai
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Building Blocks ◽  
Active Pharmaceutical Ingredients ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Pharmaceutical Ingredients ◽  
New Strategies ◽  
Made In

Functionalized tetrahydropyran (THP) rings are important building blocks and ubiquitous scaffolds in many natural products and active pharmaceutical ingredients (API). Among various established methods, the Prins reaction has emerged as a powerful technique in the stereoselective synthesis of the tetrahydropyran skeleton with various substituents, and the strategy has further been successfully applied in the total synthesis of bioactive macrocycles and related natural products. In this context, hundreds of valuable contributions have already been made in this area, and the present review is intended to provide the systematic assortment of diverse Prins cyclization strategies, covering the literature reports of the last twenty years (from 2000 to 2019), with an aim to give an overview on exciting advancements in this area and designing new strategies for the total synthesis of related natural products.

scholarly journals ZnAlMCM-41; a very ecofriendly and reusable solid acid catalyst for highly selective synthesis of 1, 3-dioxanes by Prins cyclization of olefins

2021 ◽  
Author(s):  
Manickam Selvaraj ◽  
Mohammed A. Assiri ◽  
Hari Singh ◽  
Jimmy Nelson Appaturi ◽  
Subrahmanyam Ch ◽  
...  
Keyword(s):  
Liquid Phase ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Selective Synthesis ◽  
Comparison Study ◽  
Catalytic Method ◽  
Prins Cyclization ◽  
Heterogeneous Catalytic

Prins cyclization of styrene (SE) with paraformaldehyde (PFCHO) was conducted with mesoporous ZnAlMCM-41 catalysts for synthesis of 4-phenyl-1,3-dioxane (4-PDO) under a liquid phase heterogeneous catalytic method. For comparison study, the...

ChemInform Abstract: A MODIFIED PRINS REACTION APPLICABLE TO CONJUGATED DIENES

1974 ◽  
Vol 5 (34) ◽  
pp. no-no
Author(s):  
JAN J. S. BAJOREK ◽  
RETO BATTAGLIA ◽  
GRAHAM PRATT ◽  
JAMES K. SUTHERLAND
Keyword(s):  
Conjugated Dienes ◽  
Prins Reaction

THE PRINS REACTION WITH β,γ-UNSATURATED ACIDS AND AMIDES

1957 ◽  
Vol 35 (7) ◽  
pp. 673-676 ◽  
Author(s):  
B. Belleau
Keyword(s):  
Trifluoroacetic Acid ◽  
Prins Reaction ◽  
Acid Catalyzed

The acid catalyzed condensation of cyclohexenylacetic acid and its corresponding N-methylamide with formaldehyde was investigated. Good yields of the expected δ-lactone (V) or δ-lactam (IX) were obtained when trifluoroacetic acid was used both as catalyst and solvent for the reaction.

Transformation of betulin diacetate by the Prins reaction

2008 ◽  
Vol 34 (4) ◽  
pp. 480-482 ◽  
Author(s):  
A. V. Rybina ◽  
I. S. Shepelevich ◽  
R. F. Talipov ◽  
F. Z. Galin ◽  
L. V. Spirikhin
Keyword(s):  
Prins Reaction ◽  
Betulin Diacetate
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