Diastereoselective cycloaddition of chiral 1-acryloyl-2-imidazolidinone and o-quinodimethane generated by reduction of 1,2-bis(bromomethyl)benzene with zinc |
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| Institution: | Department of Biotechnology, Faculty of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan |
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| Abstract: | The reduction of 1,2-bis(bromomethyl)benzene with zinc powder followed by cycloaddition with the chiral dienophile (4R,5S)-1-acryloyl-3,4-dimethyl-5-phenyl-2-imidazolidinone in the presence of BF3·Et2O under ultrasound irradiation gave the corresponding Diels–Alder cycloadduct in high yield (90%) and high diastereoselectivity (R:S = 87:13). |
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