Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers.
Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.
Avetta
Christopher T
CT
Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
Konkol
Leah C
LC
Taylor
Carla N
CN
Dugan
Karen C
KC
Stern
Charlotte L
CL
Thomson
Regan J
RJ
D002244:Carbon / Q000737:chemistry; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D003512:Cyclohexanones; D004987:Ethers; D007659:Ketones; C036468:cyclohexanone; D002244:Carbon