193071-28-2

Upstream product

• 261511-14-2 [(1S)-trans-1-(4-Benzyloxymethylcyclopent-2-en-1-yloxy)ethenyloxy] tert-butyldimethylsilane 
• 193071-26-0 (1S)-trans-4-Benzyloxymethylcyclopent-2-en-1-yl acetate 
• 193141-49-0 (1R)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol 
• 138382-29-3 (1R,4S)-4-(hydroxymethyl)cyclopent-2-enol 
• 193071-27-1 (1S)-trans-(5-Benzyloxymethylcyclopent-2-en-1-yl)acetic acid 

Downstream Products

• 35761-79-6 (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one 

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.