35519-24-5Relevant academic research and scientific papers
Chemoselective Synthesis of Z-Olefins through Rh-Catalyzed Formate-Mediated 1,6-Reduction
Dada, Raphael,Wei, Zhongyu,Gui, Ruohua,Lundgren, Rylan J.
supporting information, p. 3981 - 3984 (2018/03/21)
Z-olefins are important functional units in synthetic chemistry; their preparation has thus received considerable attention. Many prevailing methods for cis-olefination are complicated by the presence of multiple unsaturated units or electrophilic functio
Catalytic, Enantioselective β-Protonation through a Cooperative Activation Strategy
Wang, Michael H.,Barsoum, David,Schwamb, C. Benjamin,Cohen, Daniel T.,Goess, Brian C.,Riedrich, Matthias,Chan, Audrey,Maki, Brooks E.,Mishra, Rama K.,Scheidt, Karl A.
, p. 4689 - 4702 (2017/05/12)
The NHC-catalyzed transformation of unsaturated aldehydes into saturated esters through an organocatalytic homoenolate process has been thoroughly studied. Leveraging a unique “Umpolung”-mediated β-protonation, this process has evolved from a test bed for homoenolate reactivity to a broader platform for asymmetric catalysis. Inspired by our success in using the β-protonation process to generate enals from ynals with good E/Z selectivity, our early studies found that an asymmetric variation of this reaction was not only feasible, but also adaptable to a kinetic resolution of secondary alcohols through NHC-catalyzed acylation. In-depth analysis of this process determined that careful catalyst and solvent pairing is critical for optimal yield and selectivity; proper choice of nonpolar solvent provided improved yield through suppression of an oxidative side reaction, while employment of a cooperative catalytic approach through inclusion of a hydrogen bond donor cocatalyst significantly improved enantioselectivity.
The use of radical decarboxylation in the preparation of 1-methylcarbapenem antibiotic precursors from D-glucosamine
Anaya,Barton,Cruz Caballero,Gero,Grande,Laso,Hernando
, p. 2137 - 2140 (2007/10/02)
The stereocontrolled synthesis of optically active 1-methylcarbapenams has been performed by radical cyclization and radical decarboxylation. 1,3,4-Trisubstituted 2-azetidinones, prepared by the Staudinger reaction with D-glucosamine as chiral auxiliary and sorbic acid were used as starting materials.
