Asymmetric Diels–Alder Reaction of α‐Substituted and β,β‐Disubstituted α,β‐Enals via Diarylprolinol Silyl Ether for the Construction of All‐Carbon Quaternary Stereocenters |
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| Authors: | Prof. Dr. Yujiro Hayashi Dr. Bojan P. Bondzic Tatsuya Yamazaki Yogesh Gupta Shin Ogasawara Prof. Dr. Tohru Taniguchi Prof. Dr. Kenji Monde |
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| Affiliation: | 1. http://www.ykbsc.chem.tohoku.ac.jp;2. Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, Japan;3. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, Japan;4. Faculty of Advanced Life Science, Frontier Research Center for Advanced Material and Life Science, Hokkaido University, Kita 21 Nishi 11, Sapporo, Japan |
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| Abstract: | The asymmetric Diels–Alder reaction of α‐substituted acrolein proceeds in the presence of the trifluoroacetic acid salt of trifluoromethyl‐substituted diarylprolinol silyl ether to afford the exo‐isomer with both excellent diastereoselectivity and high enantioselectivity. In the Diels–Alder reaction of a β,β‐disubstituted α,β‐unsaturated aldehyde, good exo‐selectivity and excellent enantioselectivity was obtained when the perchloric acid salt of the bulky triisopropyl silyl ether of trifluoromethyl substituted diarylprolinol was employed as an organocatalyst in the presence of water. In both cases, all‐carbon quaternary stereocenters are constructed enantioselectively. |
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| Keywords: | all-carbon quaternary stereocenter asymmetric reaction chirality Diels– Alder reaction organocatalysis |
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