Further Information
Literature
Related Reactions
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
Recent Literature
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.
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.
