49653-17-0Relevant articles and documents
Evaluation of several routes to advanced pregabalin intermediates: Synthesis and enantioselective enzymatic reduction using ene-reductases
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)
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.
Synthesis and enantioselective hydrogenation of α-acyloxyacrylates
Schmidt,Langner,Kirschbaum,Braun
, p. 1138 - 1140 (2007/10/02)
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.
α-BROMO-α-ETHOXY-ACETIC DERIVATIVES AS NEW ALKYLATING REAGENTS
Klemm, D.,Geschwend, G.
, p. 1431 - 1438 (2007/10/02)
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.
