The rationale for stereoinduction in conjugate addition to alkylidenemalonates bearing a menthol-derived chiral auxiliary

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Use this link to cite this item : https://repo.lib.tokushima-u.ac.jp/117124

ID	117124
Author	Yamada, Ken-ichi Tokushima University Tokushima University Educator and Researcher Directory Fujiwara, Shinichi Tokushima University\|Kyoto University Inokuma, Tsubasa Tokushima University Tokushima University Educator and Researcher Directory KAKEN Search Researchers Sugano, Masayuki Tokushima University Yamaoka, Yousuke Kyoto University Takasu, Kiyosei Kyoto University
Keywords	8-Phenylmenthyl chiral auxiliary Dimethylzinc Asymmetric radical addition Benzylidenemalonate Tetramethyldioxola
Content Type	Journal Article
Description	Density-functional theory (DFT) calculations provided a new model to rationalize the stereoselectivity in the asymmetric addition to alkylidenemalonate bearing 8-phenylmentyl groups as a chiral auxiliary. The diastereoselectivity in the addition reactions of a tetramethyldioxolanyl radical with various alkyl 8-phenylmentyl benzylidenemalonates strongly supports the proposed model.
Journal Title	Tetrahedron
ISSN	00404020
NCID	AA00861787 AA11539786
Publisher	Elsevier
Volume	91
Start Page	132220
Published Date	2021-05-24
Rights	© 2021. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
EDB ID	375859
DOI (Published Version)	10.1016/j.tet.2021.132220
URL ( Publisher's Version )	https://doi.org/10.1016/j.tet.2021.132220
FullText File	tet_91_132220.pdf 595 KB
language	eng
TextVersion	Author
departments	Pharmaceutical Sciences