Synthesis of Enantiomerically Pure 4‑Hydroxy-2-cyclopentenones

Conversion of furfuryl alcohol to 4-hydroxy-2-cyclo­pentenone was studied in a microreactor channel of 0.5 mm diameter and 1.5 m length. Addition of 1 M N-methylpyrrolidinone as a cosolvent significantly reduces the polymeric material normally formed during the reaction in purely aqueous solution. T...

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Bibliographic Details
Published in:Organic process research & development 2013-12, Vol.17 (12), p.1526-1530
Main Authors: Kumaraguru, Thenkrishnan, Babita, Panuganti, Sheelu, Gurrala, Lavanya, Kuna, Fadnavis, Nitin W
Format: Article
Language:English
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Summary:Conversion of furfuryl alcohol to 4-hydroxy-2-cyclo­pentenone was studied in a microreactor channel of 0.5 mm diameter and 1.5 m length. Addition of 1 M N-methylpyrrolidinone as a cosolvent significantly reduces the polymeric material normally formed during the reaction in purely aqueous solution. The reaction follows pseudo-first-order kinetics at constant pressure (200 bar) with the values of ΔH ⧧ = 18 ± 2 kcal/mol and ΔS ⧧ = −38 ± 3 cal/mol/K. At 240 °C, 200 bar pressure, and residence time of 1.5 min, the product is obtained with 98% conversion and is isolated as a stable O-phenylacetyl derivative in 80% yield. This racemic mixture was resolved into enantiomerically pure forms by kinetic resolution with penicillin G acylase (E.C.3.5.1.11) immobilized on epoxy-activated polymer in 90–92% theoretical yield and >99% ee.
ISSN:1083-6160
1520-586X
DOI:10.1021/op400266k