120052-51-9

Upstream product

• 7129-41-1 6-oxabicyclo<3.1.0>hex-2-ene 
• 108-95-2 phenol 
• 7129-41-1 6-oxabicyclo[3.1.0]hex-2-ene 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 108-22-5 Isopropenyl acetate 
• 103056-56-0 (+/-)-cis-4-phenyloxy-2-cyclopenten-1-ol 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 169872-81-5 (1S,4R)-cis-1-phenoxy-2-cyclopentene-4-ol 
• 148969-52-2 (-)-(1S,4R)-4-phenyloxy-2-cyclopenten-1-yl acetate 
• 210701-09-0 1-acetoxy-4-phenoxy-2-cyclopentene 
• 148917-41-3 Acetic acid (3aR,4S,6R,6aS)-2,2-dimethyl-6-phenoxy-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester 
• 104010-72-2 (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of a versatile cyclopentenone: (+)-(3aS,6aS)-2,2-dimethyl-3aβ,6aβ-dihydro-4H-cyclopenta-1,3-dioxol- 4-one

The title cyclopentenone has been prepared by enzymatic resolution of cis-4-phenyloxy- and cis-4-(4-methoxyphenyloxy)-cyclopent-2-en-1-ol in isopropenyl acetate using Pseudomonas cepacia lipase. The use of a 4-methoxyphenyloxy-alcohol intermediate enabled the use of both enzymatically resolved enantiomers in the synthesis of the desired (+)-enone.

Chemoenzymatic synthesis of trans-4,5-dihydroxycyclopent-2-enones: Conversion to D-1-deoxynojirimycin

(4R,5S)-trans-4,5-Bis(tert-butyldimethylsilyloxy)cyclopent-2-enone 8 and (4R,5S)-trans-4,5-di(benzyloxy)cyclopent-2-enone 20 are prepared by equilibration of the corresponding cis derivatives; enone 8 is transformed into the glucosidase inhibitor, D-1-deoxynojirimycin 14.

A PALLADIUM-CATALYZED ROUTE TO MONO- AND DIPROTECTED CIS-2-CYCLOPENTENE-1,4-DIOLS

The ?-allylpalladium complex arising from cyclopentadiene monoepoxide has been shown to react with carboxylic acids and derivatives both as a nucleophile and an electrophile.This reaction represents an attractive synthetic route to protected versions of cis-2-cyclopentene-1,4-diol.