106732-15-4Relevant academic research and scientific papers
Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase
Deardorff, Donald R.,Amador, Roberto B.,Morton, James W.,Kim, Henry Y.,Taniguchi, Cullen M.,Balbuena, Arnel A.,Warren, Sam A.,Fanous, Vadim,Choe, S. W. Tina
, p. 2139 - 2152 (1999)
Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth.
A Facile Chemoenzymatic Route to Optically Pure Building Blocks for Cyclopentanoid Natural Products
Laumen, Kurt,Schneider, Manfred P.
, p. 1298 - 1299 (1986)
Compound (1R,4S)-(4a), a central chiral building block for cyclopentanoid natural products, was prepared in high yield and optically pure by enantioselective hydrolysis of (5a) in the presence of several lipases, and was further transformed into (R)-(1a), (1R,5S)- and (1S,5R)-(2), (7), and (8), important synthons for this class of compounds.
4-Hydroxycyclopent-2-en-1-one and derivatives as chiral synthetic equivalents of cyclopentadienone in asymmetric Diels-Alder reactions
Dols,Klunder,Zwanenburg
, p. 8515 - 8538 (2007/10/02)
Endo-tricyclodecadienone 8a and related annelated-cyclopentenones (8b, 20, 21a-c and 22) are synthesized in good chemical yield by a Diels-Alder reaction of 4-hydroxycyclo-pent-2-en-1-one 12a and derivatives 12b-h with an appropriate diene. These additions are considerably accelerated by Lewis catalysts, high pressure and by using water as solvent. Due to opposing steric and electronic effects the diastereofacial selectivity of the asymmetric cycloadditions is moderate. By carefully choosing the substrate and reaction conditions an acceptable π-facial selectivity can be achieved.
