Synthesis of trans-2,6-Disubstituted Cyclohexanones through Allylic Substitution

Abstract

trans-2,6-Disubstituted cyclohexanones were synthesized with high regio- and stereoselectivity by allylic substitution followed by ozonolysis. Both alkyl and aryl groups were successfully installed to the cyclohexane ring. The stereochemistry of the SN2' products was determined to be controlled by the pre-existing chirality on the ring. The present method is highlighted by the synthesis of enantiomerically enriched cyclohexanones.

Derivatization of Secondary Aliphatic Alcohols to Picolinates – A New Option for HPLC Analysis with Chiral Stationary Phase

“…[7][8][9] Chelation of the carbonyl oxygen and the pyridyl nitrogen in the picolinoxy moiety to MgBr 2 , produced in situ from…”

A Mild Method for the Generation and Interception of 1,2-Cycloheptadienes with 1,3-Dipoles

“…We found that the necessary allylic silane 10 was accessible via a short sequence from bromoenone 2 (Scheme ). 1,2-Reduction of the ketone under Luche conditions was followed by activation of the resulting allylic alcohol as the corresponding carbonate. Treatment of this intermediate with silyl cuprate reagent resulted in efficient conversion to 10 .…”