-Hydroxy nitriles: Chelation-controlled cyclizations

ORGN 143

Fraser F. Fleming, flemingf@duq.edu, Brian C Shook, Moshfiqur Raman, and Viet Anh Vu, vuv@duq.edu. Department of Chemistry, Duquesne University, 600 Forbes Ave, Pittsburgh, PA 15282
Chelation dramatically controls the cyclizations of -hydroxy nitriles. Double deprotonation with excess of lithium diethylamide generates a dimetalated nitrile in which chelation allows selective access to cis- and trans-decalins. The presentation will explore the fundamental control element in these cyclizations and the potential for selectivity assembling cis- and trans-hydrindanes.