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Alder-Ene 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, Synthesis, 2008, 395-400.


Rhenium(VII) Catalysis of Prins Cyclization Reactions
K. Tadpetch, S. D. Rychnovsky, Org. Lett., 2008, 10, 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, Synthesis, 2004, 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.


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., 2007, 9, 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., 2008, 73, 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., 2007, 72, 7420-7422.


Brřnsted Acid-Mediated Stereoselective Cascade Construction of Functionalized Tetrahydropyrans from 2-(Arylmethylene)cyclopropylcarbinols and Aldehydes
G.-Q. Tian, M. Shi, Org. Lett., 2007, 9, 2405-2408.