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

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

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.; Jua...

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Veröffentlicht in:Organic letters 2010-12, Vol.12 (23), p.5402-5405
Hauptverfasser: Shi, Zugui, Tan, Bin, Leong, Wendy Wen Yi, Zeng, Xiaofei, Lu, Min, Zhong, Guofu
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Crystallography, X-Ray
Cyclization
Isoxazoles - chemistry
Models, Molecular
Molecular Structure
Oxides - chemical synthesis
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102181r