4.8 Article

Catalytic Asymmetric Formal [4+1] Annulation Leading to Optically Active cis-Isoxazoline N-Oxides

Journal

ORGANIC LETTERS
Volume 12, Issue 23, Pages 5402-5405

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol102181r

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Funding

  1. Ministry of Education in Singapore [ARC12/07, T206B3225]
  2. Nanyang Technological University (URC) [RG53/07]

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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 alpha-iodoaldehydes.

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