7510-76-1Relevant academic research and scientific papers
Iron(II)-catalyzed asymmetric epoxidation of trisubstituted α,β-unsaturated esters
Luo, Lan,Yamamoto, Hisashi
, p. 7803 - 7805 (2015/02/02)
The asymmetric epoxidation of trisubstituted α,β-unsaturated esters was developed. The oxidation utilizes a pseudo-C2-symmetric iron(II) catalyst [Fe(L)2(CH3CN)(OTf)](OTf) (Tf = trifluoromethylsulfonyl) and pera
Highly enantioselective iridium-catalyzed hydrogenation of α,β-unsaturated esters
Li, Jia-Qi,Quan, Xu,Andersson, Pher G.
supporting information, p. 10609 - 10616 (2012/11/07)
α,β-Unsaturated esters have been employed as substrates in iridium-catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic- and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural products and pharmaceuticals. Asymmetric hydrogenation: A variety of α,β-unsaturated esters were hydrogenated with high enantioselectivities (see scheme). The hydrogenated products have been used in synthetic transformations as well as in formal total syntheses. Copyright
Diastereoselective synthesis of 3,4-disubstituted 5-(p-tolylsulfinyl)-5,6- dehydropiperidin-2-ones: Chirality transfer in the enantioselective synthesis of ethyl (+)-(3S,4aS,7aS)-1-oxo-octahydro-1H-cyclopenta[c]pyridine-3-carboxylate
Acherki, Hassan,Alvarez-Ibarra, Carlos,Lujan, Juan F. Collados,Quiroga-Feijoo, Maria L.
, p. 4034 - 4044 (2007/10/03)
The base-mediated reaction of enantiomerically pure α- sulfinylketimine (+)-1 with (E)-α,β-disubstituted propenoate esters afforded 3,4-disubstituted-5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones 9α-13α and 14 with high or complete diastereoselectivity. A sole diastereomer of the four possible ones, with regard to the nature of ester, was isolated, which revealed the stereocontrol of the chiral sulfinyl group in the Michael reaction and transenolization steps. In addition, the enantioselective synthesis of ethyl (+)-(3S,4aS,7aS)-1-oxo-octahydro-1H-cyclopenta[c]pyridine-3- carboxylates (+)-17α is described (five steps; 47% yield; ee ≥97%). The absolute configuration of stereocentres introduced in (+)-17α was assigned on the basis of 1H NMR data.
