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.; Juaristi, E. Tetrahedron 2008, 64, 9992), via an elegant formal [4 + 1] annulation strategy using readily available 2-nitroacrylates and α-iodoaldehydes.
Shi
Zugui
Z
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371.
Tan
Bin
B
Leong
Wendy Wen Yi
WW
Zeng
Xiaofei
X
Lu
Min
M
Zhong
Guofu
G
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007555:Isoxazoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010087:Oxides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007555:Isoxazoles; D010087:Oxides