Syn- and Anti-Selective Prins Cyclizations of δ,ε-Unsaturated Ketones to 1,3-Halohydrins with Lewis Acids

• Published in: Journal of organic chemistry Vol. 71; no. 4; pp. 1493 - 1501
• Main Authors: Miles, R. Brandon, Davis, Chad E, Coates, Robert M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.02.2006; Amer Chemical Soc
• Subjects: Acids; Alcohols - chemical synthesis; Chemistry; Chemistry, Organic; Chlorohydrins - chemical synthesis; Cyclization; Cycloparaffins; Ketones - chemistry; Physical Sciences; Science & Technology; Stereoisomerism; EPOXIDES; KETONES; ALDEHYDE; DIASTEREOSELECTIVE SYNTHESIS; PI-CYCLIZATIONS; STEREOCHEMISTRY; ALPHA; COPE REARRANGEMENT

Ten acyclic and monocyclic δ,ε-unsaturated ketones, with and without methyl substituents on the double bond, underwent halide-terminated Prins (halo-Prins) cyclizations under anhydrous conditions in the presence of Lewis acids. TiCl4, TiBr4, BCl3, and BBr3 promoted syn-selective cyclizations to ster...