Subscribe to RSS
DOI: 10.1055/s-0039-1691614
Predictive Analysis to Expand the Heterocycle Scope of the Catalytic Asymmetric Minisci Reaction
Publication History
Publication Date:
21 January 2020 (online)
Key words
Minisci reaction - chiral phosphoric acids - multivariate linear regression - diazines - asymmetric catalysis
Significance
The Phipps group, in collaboration with the Sigman group, presents a multivariate linear regression analysis to gain a better understanding of the structural features controlling the regio- and stereoselectivity in their recently reported catalytic asymmetric Minisci reaction of redox-active esters with pyridines/quinolines (Science 2018, 360, 419). The generated mathematical model was also found to predict accurately the outcome of the reaction when new types of heteroarenes (pyrimidines or pyrazines) are used as substrates.
#
Comment
Since its discovery, the Minisci reaction has become one of the most widely used transformations for C–C bond formation onto heteroarenes. However, to date, only a few asymmetric examples have been reported. Following their previous work on quinolines/pyridines, the authors present an accurate model that relates steric and electronic parameters (of both catalyst and product) to the enantioselectivity of the process. These analyses are quite desirable in asymmetric catalysis to predict the performance of new substrate types, thereby permitting a rapid expansion of scope.
#
#