Ring expansion/homologation--aldehyde condensation cascade using tert-trihalomethylcarbinols.
Treatment of cyclic tert-trihalomethylcarbinols with CrCl(2) in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.
Falck
J R
JR
Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA. j.falck@utsouthwestern.edu
He
Anyu
A
Reddy
L Manmohan
LM
Kundu
Abhijit
A
Barma
Deb K
DK
Bandyopadhyay
A
A
Kamila
Sukanta
S
Akella
Radha
R
Bejot
Romain
R
Mioskowski
Charles
C
D000447:Aldehydes / Q000737:chemistry*; D003500:Cyclization; D000432:Methanol / Q000737:chemistry*
D000447:Aldehydes; D000432:Methanol