Evaluation of several routes to advanced pregabalin intermediates: Synthesis and enantioselective enzymatic reduction using ene-reductases
This publication describes the evaluation of four synthetic routes to the advanced pregabalin (Lyrica) intermediate 7. Asymmetric reduction of (E)-7 with an ene-reductase (OPR1 from Lycopersicon esculentum) gave a saturated cyanoester intermediate 5 with the desired S stereocenter in ≥99% ee. OPR1 also catalyzed the reduction of (Z)-7 to (S)-5, but with lower conversion and selectivity.
Debarge, Sebastien,McDaid, Paul,O'Neill, Pat,Frahill, James,Wong, John W.,Carr, Donncha,Burrell, Adam,Davies, Simon,Karmilowicz, Mike,Steflik, Jeremy
p. 109 - 121
(2014/05/20)
CROSSLINKING AGENT, CROSSLINKED POLYMER, AND USES THEREOF
There is provided a novel crosslinking agent for use in crosslinked polymer fabrication, specifically a crosslinking agent containing at least one compound selected from glyoxylate and a glyoxylic acid ester derivative represented by the following general formula (1): wherein R1 and R2 each independently represents an alkyl group having 1 to 10 carbon atoms and R3 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
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Page/Page column 20
(2010/08/22)
Synthesis and enantioselective hydrogenation of α-acyloxyacrylates
Numerous α-acyloxyacrylates have been prepared by Wittig-Horner reaction of aldehydes and ethyl 2-acyloxy-2-(diethoxyphosphoryl)acetates which were easily obtained from glyoxylic acid hydrate. The formed α-acyloxyacrylates were subsequently hydrogenated enantioselectively using Rh-DIPAMP and Ru-BINAP (ee = 82-98%) to furnish the corresponding α-acyloxycarboxylates.
Schmidt,Langner,Kirschbaum,Braun
p. 1138 - 1140
(2007/10/02)
ENZYLATICALLY CLEAVABLE ALKOXYCARBONYL ETHOXYMETHYL ESTERS FOR REVERSIBLE BLOCKING OF CARBOXYL GROUPS
By O-alkylation carboxylic acids with α-bromo-α-ethoxy acetates new alkoxycarbonyl ethoxymethyl esters (ACEM esters) were synthesised in a simple route.The ACEM blocking group can be casily cleft by esterases.
Klemm, D.,Geschwend, G.
p. 2337 - 2348
(2007/10/02)
α-BROMO-α-ETHOXY-ACETIC DERIVATIVES AS NEW ALKYLATING REAGENTS
A convenient synthesis of new α-bromo-α-ethoxy-acetic acid alkylating reagents, intermediates for the synthesis of enzymatically cleavable alkoxycarbonyl ethoxymethyl esters, is described.
Klemm, D.,Geschwend, G.
p. 1431 - 1438
(2007/10/02)
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