Synthesis of trans-2,6-disubstituted cyclohexanones through allylic substitution.
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.
Department of Bioengineering, Tokyo Institute of Technology , Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Yuichi
Y
Kobayashi
Chao
C
Feng
Atsushi
A
Ikoma
Narihito
N
Ogawa
Takayuki
T
Hirotsu
D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D003512:Cyclohexanones