94348-75-1Relevant articles and documents
Pd-Catalyzed Cascade Reactions of Aziridines: One-Step Access to Complex Tetracyclic Amines
Booker-Milburn, Kevin I.,Knowles, Jonathan P.,Latter, Francesca,Schwarz, Maria,Steeds, Hannah G.
supporting information, p. 4986 - 4990 (2021/07/19)
The combination of palladium catalysis and thermal cycloaddition is shown to transform tricyclic aziridines into complex, stereodefined tetracyclic products in a single step. This highly unusual cascade process involves a diverted Tsuji-Trost sequence leading to a surprisingly facile intramolecular Diels-Alder reaction. The starting materials are accessible on multigram scales from the photochemical rearrangement of simple pyrroles. The tetracyclic amine products can be further elaborated through routine transformations, highlighting their potential as scaffolds for medicinal chemistry.
Bioreduction of α-Acetoxymethyl Enones: Proposal for an SN2′ Mechanism Catalyzed by Enereductase
Paula, Bruno R. S.,Zampieri, Davila,Rodrigues, J. Augusto R.,Moran, Paulo J. S.
, p. 3555 - 3571 (2016/11/25)
(Z)-3-Acetoxymethyl-4-R-3-buten-2-ones (R=aryl, alkyl) and (Z)-3-methyl-4-R-3-buten-2-ones (R=aryl) were synthesized and submitted to reduction by the yeast Saccharomyces cerevisiae producing the (R)- and (S)-4-R-3-methybutan-2-ones, respectively. This stereochemistry control strategy was applied in the syntheses of (R)- and (S)-Tropional with moderate to high enantiomeric excesses. Other (Z)-3-acyloxymethyl-4-phenyl-3-buten-2-ones showed similar behavior to the (Z)-3-acetoxymethyl counterpart, and the acylated Morita–Baylis–Hillman adduct 1-acetoxy-2-methylene-1-phenylbutan-3-one produced a mixture of products, with and without the acetoxy group, via three different reaction pathways. In addition to experiments employing whole cells, those in which isolated enereductases were used suggested that the main pathway through which the loss of the acetoxy group occurs during the biocatalytic cascade is an SN2′-type reaction, rather than formal hydrogen addition followed by acetic acid elimination. Finally, related ethyl enones were reduced enantioselectively by the yeast Candida albicans, producing both (R)- and (S)-reduction products, depending on the presence of the acetoxy group in the starting material. (Figure presented.).
Enantioselective allylic substitution of Morita-Baylis-Hillman adducts catalyzed by planar chiral [2.2]paracyclophane monophosphines
Zhang, Tang-Zhi,Dai, Li-Xin,Hou, Xue-Long
, p. 1990 - 1994 (2008/02/13)
Planar chiral [2,2]cyclophane monophosphines are efficient catalyst in the reaction of Morita-Baylis-Hillman adducts with phthalimide. The corresponding allylic substituted products were afforded in high yields and in good to moderate ee.