934986-75-1

Upstream product

• 261511-14-2 [(1S)-trans-1-(4-Benzyloxymethylcyclopent-2-en-1-yloxy)ethenyloxy] tert-butyldimethylsilane 
• 3587-60-8 Benzyloxymethyl chloride 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 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 
• 100-39-0 benzyl bromide 

Downstream Products

• 934986-76-2 C₁₅H₁₈O₃ 
• 934986-78-4 C₁₅H₁₈O₃ 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure cyclopentene building blocks

An efficient synthesis of the enantiomerically pure cis-annulated cyclopentenes 2 and ent-2 was established by the use of an enzymatic transesterification and hydrolysis, respectively, followed by an S N2-type substitution with a benzyloxymethyl cuprate and a sigmatropic rearrangement. The advantage of this approach is the short sequence combined with an excellent overall yield and an enantiomeric excess of 99%. Georg Thieme Verlag Stuttgart.

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.