jo9907787_si_001.pdf (1.95 MB)
Download file[n + 1] Annulation Route to Highly Substituted Cyclic Ketones with Pendant Ketone, Nitrile, and Ester Functionality
journal contribution
posted on 31.08.1999, 00:00 authored by Robert B. Grossman, Dhananjay S. Pendharkar, Brian O. PatrickTwo carbon acids connected by a tether containing a ketone undergo two Michael reactions to
3-butyn-2-one to afford highly substituted and functionalized cyclic ketones with pendant ketone,
nitrile, and ester functionality. The stereochemical courses of the double Michael reactions vary
remarkably with the structure of the starting material. Double Michael adducts with equatorially
disposed cyano groups can be hydrogenated to afford trans-fused bicyclic amines.