Recent applications of the Prins Reaction in Stereoselective Synthesis Eileen Shaughnessy Evans Group Seminar larch 19 1999 Prins-Pinacol methodology Il. Prins-Pinacol synthese IlL Tetrahydropyran synthesis IV. Other uses of the Prins reaction in synthesis Prins reaction: Adams, D.R.; Bhaynagar, S. D. Synthesis 1977, 661 Prins and carbonyl ene reactions: Snider, B. B, Comprehensive Organic Synthesis, 1991, Vol. 2 Bicyclic THF synthesis: Dave MacMillan, Evans Group Seminar, 1996 Approaches to 2, -6-Disubstituted THP Derivatives: Duke Fitch, Evans Group Seminar, 1997 The Prins reaction X RICHO Lewis Ad Prins AlSo 32C-011/19/008:15PMPrins-Pinacol methodology Prins-Pinacol syntheses Tetrahydropyran synthesis Other uses of the Prins reaction in synthesis I. II. III. IV. Recent Applications of the Prins Reaction in Stereoselective Synthesis Eileen Shaughnessy Evans Group Seminar March 19, 1999 Prins reaction: Adams, D.R.; Bhaynagar, S. D. Synthesis 1977, 661 Prins and carbonyl ene reactions: Snider, B. B., Comprehensive Organic Synthesis, 1991, Vol. 2 Bicyclic THF synthesis: Dave MacMillan, Evans Group Seminar, 1996 Approaches to 2,-6-Disubstituted THP Derivatives: Duke Fitch, Evans Group Seminar, 1997 O R1 H R2 R1 R2 OH O O R1 R2 R2 R1 R2 OH - H+ HX R1 R2 OH X O Me O Ph Me Me Me O Ph - Cl4SnO O Ph - Cl4SnO O Ph O + The Prins Reaction R1CHO X- + + Lewis Acid >95% ee Prins pinacol Prins-Pinacol: Prins: 32C-01 1/19/00 8:15 PM