190185-60-5Relevant academic research and scientific papers
Concise synthesis of (+)-β-benzyl γ-butyrolactones from butynediol
Kamlage,Sefkow,Zimmermann,Peter
, p. 77 - 80 (2002)
The synthesis of optically active β-benzyl-γ-butyrolactones from butynediol via four transition metal catalysed reactions is reported. Key reactions are the hitherto unknown enantioselective hydrogenation of 2-benzyl-2-buten-1,4-diols using Ir(I) phosphinooxazoline catalysts and the regiocontrolled oxidation of the resulting 2-benzyl-1,4-butanediols to the β-substituted butyrolactones.
Diastereoselective conjugate addition of Grignard reagents to a homochiral fumaramide derived from Oppolzer's sultam
Reid, Gary P.,Brear, Kieron W.,Robins, David J.
, p. 793 - 801 (2004)
Conjugate addition of Grignard reagents to N,N′-fumaroylbis[(2R)- bornane-10,2-sultam] 1 occurred with moderate to high levels of diastereoselectivity. Diastereomeric excesses were estimated by analysis of the 1H NMR spectra of the succinamide mixtures and enantiomeric excesses from 19F NMR spectra of the bis Mosher esters of the diols produced by reductive cleavage of the succinamides. Saponification of the succinamides gave the corresponding (R)-succinic acids with ees up to 92% showing that addition of the Grignard reagents takes place selectively on the re-face of 1.
The absolute stereochemistry of the ester functions of fumonisin B1
Edwards, Oliver E.,Blackwell, Barbara A.,Driega, Alex B.,Bensimon, Corrine,ApSimon, John W.
, p. 4515 - 4518 (2007/10/03)
Synthesis of an optically active γ-lactone related to tricarballylic acid (TCA) and correlation of this to the same lactone derived from the two sidechain TCA esters at C-14 and C-15 of fumonisin B1 has established that these esters have the R configuration.
Oxidation of some prochiral 3-substituted cyclobutanones using monooxygenase enzymes: a single-step method for the synthesis of optically enriched 3-substituted γ-lactones
Gagnon, Rene,Grogan, Gideon,Groussain, Esther,Pedragosa-Moreau, Sandrine,Richardson, Paul F.,et al.
, p. 2527 - 2528 (2007/10/02)
Oxidation of the prochiral cyclobutanones 1-5 using Acinetobacter calcoaceticus NCIMB 9871 and Pseudomonas putida NCIMB 10007 monooxygenases (MO1 and MO2) furnishes the corresponding lactones 6-10 in moderate to excellent yield and enantiomeric purity.The
