Novel binaphthyl and biphenyl α- and β-amino acids and esters: organocatalysis of asymmetric Diels–Alder reactions. A combined synthetic and computational study

文献情報

出版日 2018-09-17

DOI 10.1039/C8OB01795F

インパクトファクター 3.876

著者

Philip C. Bulman Page, Francesca S. Kinsey, Yohan Chan, Ian R. Strutt, Alexandra M. Z. Slawin, Garth A. Jones

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要旨

Asymmetric catalysis of the Diels–Alder reaction between cyclopentadiene and cinnamaldehydes has been studied using as catalysts a range of novel α- and β-aminoacids and aminoesters with binaphthyl and biphenyl backbones, providing enantioselectivities of up to 62% ee. B3LYP/6-31G* calculations, including free energy corrections, have been carried out on a binaphthyl catalyst example to identify transition state structures and to aid in the identification of major enantiomers. The calculated product ratios agree well with the experimental data; the transition states identified involve preferential approach of cyclopentene along a trajectory adjacent to the acid/ester group. The four lowest energy transition states display a stabilizing dipolar interaction between the carbonyl group oxygen atom and a terminal proton of the diene unit.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Novel binaphthyl and biphenyl α- and β-amino acids and esters: organocatalysis of asymmetric Diels–Alder reactions. A combined synthetic and computational study

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