81956-32-3Relevant academic research and scientific papers
Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation
Shi, Chang-Yun,Eun, Jungmin,Newhouse, Timothy R.,Yin, Liang
, p. 9493 - 9499 (2021)
Catalytic asymmetric remote conjugate borylation is challenging as the control of regioselectivity is not trivial, the electrophilicity of remote sites is extenuated, and the remote asymmetric induction away from the carbonyl group is difficult. Herein, catalytic asymmetric conjugate 1,6-, 1,8- and 1,10-borylation was developed with excellent regioselectivity, which delivered α-chiral boronates in moderate to high yields with high enantioselectivity. The produced chiral boronate smoothly underwent oxidation, cross-coupling, and one-carbon homologation to give synthetically versatile chiral compounds in moderate yields with excellent stereoretention. Furthermore, a stereomechanistic analysis was conducted using DFT calculations, which provides insights into the origins of the regioselectivity. Finally, the present 1,6-borylation was successfully applied in an efficient one-pot asymmetric synthesis of (?)-7,8-dihydrokavain.
Multistep Microwave-Assisted Solvent-Free Organic Reactions: Synthesis of 4-Oxo-tetrahydro-pyridine
Panunzio, Mauro,Lentini, Maria Antonietta,Campana, Eileen,Martelli, Giorgio,Tamanini, Emiliano,Vicennati, Paola
, p. 345 - 359 (2007/10/03)
Preparation and ring-closure of 2-dimethylaminomethylene-5-substituted-3-oxo-pent-4-enoic acid benzyl esters to dihydropyridine rings are efficiently and quickly carried out under solvent-free conditions in an open-vessel microwave system. The syntheses o
Methodology for the Synthesis of Phosphorus-Activated Tetramic Acids: Applications to the Synthesis of Unsaturated 3-Acyltetramic Acids
Boeckman, Robert K.,Thomas, Anthony J.
, p. 2823 - 2824 (2007/10/02)
A general method is described for the preparation of phosphonate-activated 3-acetyltetramic acids from a variety of α-amino esters, which can serve as precursors of enoyl and dienoyl tetramic acids which are found in a number of natural products.
