20566-48-7Relevant articles and documents
Enantioselective Enzymatic Reduction of Acrylic Acids
An, Chihui,Shaw, Megan H.,Tharp, Annika,Verma, Deeptak,Li, Hongming,Wang, Heather,Wang, Xiao
supporting information, p. 8320 - 8325 (2020/11/03)
An ene-reductase (ERED 36) with broad substrate specificity was identified, and optimization studies led to the development of an enzymatic protocol for the reduction of α,β-unsaturated acids under mild, aqueous conditions. The substrate scope includes aromatic- A nd aliphatic-substituted acrylic acids, as well as cyclic α,β-substituted acrylic acids, yielding chiral α-substituted acids with exquisite levels of enantioselectivity (>99% ee).
Pd-catalyzed threefold arylation of Baylis-Hillman bromides and acetates with triarylbismuth reagents
Rao, Maddali L. N.,Giri, Somnath
, p. 4580 - 4589 (2012/11/07)
Functionalized alkyl 2-benzylacrylates and 2-benzylacrylonitriles were synthesized by means of atom-economic cross-couplings of Baylis-Hillman bromides or acetates with BiAr3 under palladium-catalyzed conditions. These reactions, involving thre
Stereoselective syntheses of 4-hydroxy 4-substituted glutamic acids
Tamura, Osamu,Shiro, Tomoya,Ogasawara, Mizuho,Toyao, Atsushi,Ishibashi, Hiroyuki
, p. 4569 - 4577 (2007/10/03)
The 4-hydroxy 4-substituted glutamic acid moiety is a common substructure of biologically important natural products such as monatin [(2S,4S)-2], lycoperdic acid (3), and dysiherbaine (4). To develop methodology for syntheses of these natural products, cycloadditions of nitrone 5 with 2-substituted 2-propen-1-ols 6 and 2-substituted acrylates 8 were investigated. Reactions of nitrone 5 with alcohols 6 in the presence of MgBr2OEt2 gave cycloadducts 7 in a highly stereoselective manner, whereas noncatalyzed reactions of 5 with acrylates 8 afforded adducts 9. Using the former reaction, syntheses of monatin [(2S,4S)-2], monatin derivative 18, and lycoperdic acid (3) were accomplished. The C4-epimer of monatin [(2S,4R)-2)] was also synthesized by employing the latter cycloaddition.