- A Straightforward Synthesis of Trideuterated α-Terpinene for Mechanistic Studies
-
Regiospecifically trideuterated (2,6,6-2H3)-α-terpinene was prepared in six steps and with a deuterium incorporation of >99 % in 24 % yield from 1,4-cyclohexanedione monoethylene ketal. The synthetic procedure involved twofold cross-coupling reactions of alkylcuprates (lithium dimethylcuprate and chloromagnesium cyano(isopropyl)cuprate, respectively) with enol triflates to introduce the alkyl substituents on the 1,3-cyclohexadiene backbone. By changing the alkylcuprates, the synthetic approach could serve as a prototype for the synthesis of various 1,4-dialkyl-substituted 1,3-cyclohexadiene derivatives, which could be deuterium-labeled as well, for example for mechanistic studies.
- Christoffers, Jens,Mitschke, Nico,Wilkes, Heinz
-
-
- Asymmetric approach toward chiral cyclohex-2-enones from anisoles via an enantioselective isomerization by a new chiral diamine catalyst
-
A 3-step asymmetric approach toward the optically active chiral cyclohex-2-enones from anisoles has been developed. The crucial asymmetric induction step is an unprecedented catalytic enantioselective isomerization of β,γ-unsaturated cyclohex-3-en-1-ones
- Lee, Jung Hwa,Deng, Li
-
supporting information
p. 18209 - 18212
(2013/01/15)
-
- Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers
-
(S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (±)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide.
- Mori, Kenji
-
p. 2133 - 2142
(2007/10/03)
-
- Michael, Michael-aldol and Michael-Michael reactions of enolate equivalents of butane-2,3-diacetal protected glycolic acid derivatives
-
Consecutive coupling reactions of butane-2,3-diacetal protected glycolic acid derivatives with Michael acceptors and aldehydes are reported. An enantiopure sample of this building block was used to kinetically resolve a chiral Michael acceptor present as a racemic mixture of enantiomers. The Royal Society of Chemistry 2005.
- Ley, Steven V.,Dixon, Darren J.,Guy, Richard T.,Rodriguez, Felix,Sheppard, Tom D.
-
p. 4095 - 4107
(2007/10/03)
-