Prins Reaction

Prins Reaction

The Prins Reaction Is The Acid-catalyzed Of Addition Aldehydes To Alkenes, And Gives Different Products Depending On The Reaction Conditions. It Can Be Thought Of Conceptually As The Addition Of The Elements Of The Gem-diol Carbonyl Hydrate Of The Aldehyde Across The Double Bond.

An Excess Of Aldehyde And Temperatures < 70 °C Lead To The Formation Of Acetals. When One Equivalent Of Aldehyde Is Used And Temperatures Are > 70 °C Diols Or Allylic Alcohols May Be Isolated.

Although The Mechanism Is Different, A Prins Allylic Alcohol Product Is Equivalent To The Result Of An Ene Reaction.


Mechanism Of The Prins Reaction

Recent Literature


The 'Aqueous' Prins Cyclization: A Diastereoselective Synthesis Of 4-Hydroxytetrahydropyran Derivatives
J. S. Yadav, B. V. S. Reddy, G. G. K. S. N. Kumar, S. Aravind, Synthesis2008, 395-400.


Rhenium(VII) Catalysis Of Prins Cyclization Reactions
K. Tadpetch, S. D. Rychnovsky, Org. Lett.200810, 4839-4842.


Lewis Acidic Chloroaluminate Ionic Liquids: Novel Reaction Media For The Synthesis Of 4-Chloropyrans
J. S. Yadav, B. V. S. Reddy, M. S. Reddy, N. Niranjan, A. R. Prasad, Eur. J. Org. Chem.2003, 1779-1783.


Rapid And Efficient Protocol For The Synthesis Of 4-Chlorotetrahydropyrans Using Niobium(V) Chloride
J. S. Yadav, B. V. Subba Reddy, M. K. Gupta, S. K. Biswas, Synthesis2004, 2711-2715.


Selective Prins Reaction Of Styrenes And Formaldehyde Catalyzed By 2,6-Di-tert-butylphenoxy(difluoro)borane
T. Bach, J. Löbel, Synthesis, 2002, 2521-2526.


A General Catalytic Asymmetric Prins Cyclization
L. Liu, P. S. J. Kaib, A. Tap, B. List, J. Am. Chem. Soc.2016138, 10822-10825.


Preparation Of trans-2-Substituted-4-halopiperidines And cis-2-Substituted-4-halotetrahydropyrans Via AlCl3-Catalyzed Prins Reaction
G.-Q. Liu, B. Cui, R. Xu, X.-M. Li, J. Org. Chem.201681, 5144-5161.


An Efficient Method Allows The Construction Of  2,6-cis-4,5-dibromo-tetrasubstituted Tetrahydropyran Rings With Well-controlled Stereochemistry In Good Yields.
F. Liu, T.-P. Loh, Org. Lett.20079, 2063-2066.


5- And 6-Exocyclic Products, cis-2,3,5-Trisubstituted Tetrahydrofurans, And cis-2,3,6-Trisubstituted Tetrahydropyrans Via Prins-Type Cyclization
S. N. Chavre, H. Choo, J. K. Lee, A. N. Pae, Y. Kim, Y. S. Cho, J. Org. Chem.200873, 7467-7471.


Tandem Bis-aldol Reaction Of Ketones: A Facile One-Pot Synthesis Of 1,3-Dioxanes In Aqueous Medium
V. Polshettiwar, R. S. Varma, J. Org. Chem.200772, 7420-7422.


Brønsted Acid-Mediated Stereoselective Cascade Construction Of Functionalized Tetrahydropyrans From 2-(Arylmethylene)cyclopropylcarbinols And Aldehydes
G.-Q. Tian, M. Shi, Org. Lett.20079, 2405-2408.