@article{oai:nakamura-u.repo.nii.ac.jp:00002670,
 author = {Uchiyama, Fumiaki and 内山, 文昭},
 issue = {11},
 journal = {中村学園大学薬膳科学研究所研究紀要, Proceedings of PAMD Institute of Nakamura Gakuen University},
 month = {Mar},
 note = {The polarity of π bond of carbonyl groups always occurs horizontally to carbonyl plane. This polarity is used as “horizontal polarity” in this paper. The horizontal polarity determines the reactivity to nucleophilic addition of carbonyl groups and is indicated as LUMO in molecular orbital method. I assume that the vertical shift of π electron density of carbonyl groups, named“vertical polarity”, occurs perpendicular to the plane of carbonyl groups by electron repulsion under the constant geometry of carbonyl atoms. The π electorn density in the vertical polarity changes perpendicular to the plane of carbonyl molecules. I propose that the big lobe caused by the vertical polarity stabilizes the overlapping with the nucleophilic electron pair in the transition state and determines the stereoselectivity in the nucleophilic addition of carbonyl groups. I show that the concept of the vertical polarity is verified from the stereoselective reduction of 4-t-butylcyclohexanone and the chiral induction at acyclic carbonyl carbons during nucleophilic additions.},
 pages = {1--5},
 title = {Stereoselectivity and vertical polarity hypothesis for carbonyl addition},
 year = {2019},
 yomi = {ウチヤマ, フミアキ}
}