Catalytic asymmetric formal [4 + 1] annulation leading to optically active cis-isoxazoline N-oxides |
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| Authors: | Shi Zugui Tan Bin Leong Wendy Wen Yi Zeng Xiaofei Lu Min Zhong Guofu |
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| Affiliation: | Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371. |
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| Abstract: | The catalytic asymmetric synthesis of densely functionalized cis-isoxazoline N-oxides was realized with novel use of an organocatalyst, (S)-2-(azidodiphenylmethyl)pyrrolidine (4e) (Tan, B.; Zhu, D.; Zhang, L.; Chua, P. J.; Zeng, X.; Zhong, G. Chem.-Eur. J. 2010, 16, 3842; Olivares-Romero, J. L.; Juaristi, E. Tetrahedron 2008, 64, 9992), via an elegant formal [4 + 1] annulation strategy using readily available 2-nitroacrylates and α-iodoaldehydes. |
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