35761-79-6

Upstream product

• 38931-62-3 (1S,5R,6S,7R)-6-benzyloxymethyl-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one 
• 53153-20-1 (1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one 
• 193071-28-2 (3aR,4S,6R,6aR)-4-Benzyloxymethyl-6-iodohexahydrocyclopenta[b]furan-2-one 
• 138382-29-3 (1R,4S)-4-(hydroxymethyl)cyclopent-2-enol 
• 193141-49-0 (1R)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol 
• 193071-26-0 (1S)-trans-4-Benzyloxymethylcyclopent-2-en-1-yl acetate 
• 193071-27-1 (1S)-trans-(5-Benzyloxymethylcyclopent-2-en-1-yl)acetic acid 
• 261511-14-2 [(1S)-trans-1-(4-Benzyloxymethylcyclopent-2-en-1-yloxy)ethenyloxy] tert-butyldimethylsilane 

Downstream Products

• 83060-94-0 (1S,2R,3S)-3-Benzyloxymethyl-2-(2-phenylselanyl-ethyl)-cyclopentanol 

Relevant academic research and scientific papers

Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols

The preparation and lithium amide-induced rearrangements of 1,2-dideuterated 4-substituted cyclopentene oxides 11 and 19 are described, providing insight into the deprotonation mechanisms operating in such systems. Highly enantioselective syntheses of 4-substituted cis-4-hydroxymethylcyclopent-2-en-1-ols 32a-c are described. Also described are asymmetric syntheses of prostaglandin precursor 40 and (+)-iridomyrmecin (48) via highly enantioselective rearrangement of the epoxide 3 and subsequent Ireland-Claisen rearrangement. The Royal Society of Chemistry 1999.

An Enantioselective Epoxide Rearrangement - Claisen Rearrangement Approach to Prostaglandins and (+)-Iridomyrmecin

The asymmetric syntheses of prostaglandin precursor 8 and (+)iridomyrmecin (12) via highly enantioselective rearrangement of the epoxide 1 and subsequent Ireland-Claisen rearrangement are described.

Asymmetric microbiological Baeyer-Villiger reaction of a bridged bicyclic ketone: Divergent behaviour of its enantiomers

The bioconversion of 7-anti-benzyloxymethylbicyclo[2.2.1]hept-5-en-2-one 1 with cells of Acinetobacter calcoaceticus NCIB 9871 has been studied. Its (1R,4S,7R) enantiomer underwent a Baeyer-Villiger oxidation yielding rearranged lactone 2 (ee 85%), whereas (1S,4R,7S)-1 was reduced to alcohols 3-endo (ee 95%) and 3-exo (o.p. 89%).