1020108-76-2Relevant academic research and scientific papers
The 'aqueous' Prins cyclization: A diastereoselective synthesis of 4-hydroxytetrahydropyran derivatives
Yadav, Jhillu S.,Subba Reddy, Basi V.,Narayana Kumar, Gunda G. K. S.,Aravind, Seema
, p. 395 - 400 (2008)
Phosphomolybdic acid (H3PMo12O40, a heteropoly acid) is found to catalyze efficiently the Prins cyclization of homoallylic alcohols with aldehydes in water at room temperature to provide tetrahydropyran-4-ol derivatives in high yields with all cis-selectivity. Only cyclic ketones can give spirocyclic products. The use of phosphomolybdic acid in water makes this procedure simple, more convenient, cost-effective, and environmentally friendly. Georg Thieme Verlag Stuttgart.
Alkyl-group selection in an acidic-surfactant-promoted reaction of homoallyl alcohols and aldehydes in water
Hatakeyama, Takanori,Chisaka, Yuki,Kuroda, Chiaki
experimental part, p. 1333 - 1340 (2009/10/16)
The hydrophobic effect in the reaction of a homoallyl alcohol with an aldehyde (Yadav's reaction system) under aqueous conditions in the presence of an acidic surfactant was studied indicating the presence of the alkyl-substituent effect, although not a dramatic one. The DBSA-promoted reaction proceeds relatively faster when both the homoallyl alcohol and the aldehyde carry a cycloalkyl group (DBSA=4-dodecylbenzenesulfonic acid). In contrast, the reaction of the substrates having an unbranched alkyl group is relatively more favorable in SDS/HCl than in DBSA (SDS=sodium dodecyl sulfate).
