TY - JOUR
T1 - [n + 1] Annulation route to highly substituted cyclic ketones with pendant ketone, nitrile, and ester functionality
AU - Grossman, Robert B.
AU - Pendharkar, Dhananjay S.
AU - Patrick, Brian O.
PY - 1999/9/17
Y1 - 1999/9/17
N2 - Two 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.
AB - Two 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.
UR - https://www.scopus.com/pages/publications/0033578687
UR - https://www.scopus.com/pages/publications/0033578687#tab=citedBy
U2 - 10.1021/jo9907787
DO - 10.1021/jo9907787
M3 - Article
AN - SCOPUS:0033578687
SN - 0022-3263
VL - 64
SP - 7178
EP - 7183
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -