Quantifying Structural Effects of Amino Acid Ligands in Pd(II)-Catalyzed Enantioselective C-H Functionalization Reactions

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Title
Quantifying Structural Effects of Amino Acid Ligands in Pd(II)-Catalyzed Enantioselective C-H Functionalization Reactions
Author(s)
Yoonsu Park; Zachary L. Niemeyer; Jin-Quan Yu; Matthew S. Sigman
Publication Date
2018-01
Journal
ORGANOMETALLICS, v.37, no.2, pp.203 - 210
Publisher
AMER CHEMICAL SOC
Abstract
Delineating complex ligand effects on enantioselectivity is a longstanding challenge in asymmetric catalysis. With α-Amino acid ligands, the essential difficulty lies in accurately describing integrated perturbations induced by simultaneous variation about the α side chain and N protecting group of the ligand, which hampers an intuitive understanding of the structure-enantioselectivity relationships. To deconvolute such complexity in chiral amino acid enabled enantioselective C-H functionalization reactions, a computational organometallic model system was developed. Whereas a model based only on a conventional results in diminished predictive power, the ground state Pd(II)-based models display an excellent ability to describe the observed enantioselectivity. These structures were leveraged using a multivariate modeling approach to successfully describe Pd(II)-catalyzed C-H alkylation, alkenylation, and two C-H arylation reactions, wherein descriptors of torsion angle, percent buried volume, and NBO charge showed quantitative relevance to predict enantiomeric excess. On the basis of the insights revealed in these case studies, an optimal set of amino acid ligands is suggested to provide maximum information in a screening campaign. © 2017 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/4727
ISSN
0276-7333
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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