225779-46-4

Upstream product

• 865780-25-2 methyl 6-hydroxy-cyclohex-1-enecarboxylate 
• 79-22-1 methyl chloroformate 

Downstream Products

• 869369-08-4 (R)-(+)-methyl 6-(4-methoxyphenoxy)cyclohex-1-encarboxylate 
• 932743-56-1 (6S)-6-(4-methoxybenzylamino)cyclohex-1-enecarboxylic acid methyl ester 
• 932743-49-2 6-benzylamino-cyclohex-1-enecarboxylic acid methyl ester 
• 1041370-21-1 (R)-2-methoxycarbonyl-2-cyclohexen-1-ylmalonic acid dibenzyl ester 
• 1062574-10-0 C₂₂H₂₅NO₅S 
• 1062573-42-5 6-(4-tert-butylphenylamino)cyclohex-1-enecarboxylic acid methyl ester 
• 1062573-45-8 6-(3-methoxyphenylamino)cyclohex-1-enecarboxylic acid methyl ester 
• 1062573-44-7 6-(4-chlorophenylamino)cyclohex-1-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Pd-catalyzed asymmetric allylic alkylation of 2-substituted cycloalkenyl carbonates using a chiral diaminophosphine oxide: (S,RP)-Ph-DIAPHOX

A Pd-catalyzed asymmetric allylic alkylation of 2-substituted cycloalkenyl carbonates using a chiral diaminophosphine oxide is described. Asymmetric allylic substitution of various cyclic substrates proceeded using 5 mol % of Pd catalyst, 10 mol % of (S,R

Pd-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman adduct derivatives using chiral diaminophosphine oxides: DIAPHOXs

(Chemical Equation Presented) Asymmetric allylic animation of allylic carbonates prepared from racemic Morita-Baylis-Hillman adducts proceeded in the presence of Pd catalyst, chiral diaminophosphine oxide (DIAPHOX), and BSA, affording the corresponding chiral aza-Morita-Baylis-Hillman adduct derivatives in excellent yield with up to 99% ee. The cyclic reaction products could be converted into various synthetically useful compounds such as chiral cyclic β-amino acids.

Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine

An efficient divergent synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges by employing a Pd-catalyzed asymmetric allylic alkylation (AAA) to set the stereochemistry. Three generations of syntheses of galanthamine are discussed in detail with particular focus on the scope of the palladium-catalyzed AAA reactions and intramolecular Heck reactions. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine could be formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine.