Asymmetric Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Imines for the Synthesis of Chiral Spiro-Pyrazoline-Oxindoles

作者：Wang, Gang; Liu, Xiaohua; Huang, Tianyu; Kuang, Yulong; Lin, Lili; Feng, Xiaoming^*

来源：Organic Letters, 2013, 15(1): 76-79.

DOI：10.1021/ol303097j

• HIGHLY ENANTIOSELECTIVE SYNTHESIS
• AZOMETHINE IMINES
• NITRONES
• YLIDES
• CONSTRUCTION
• DIAZOESTERS
• ISATINS
• KETONES

A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)(2) complex of an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1,3-dipole in the construction of 2-pyrazoline subunit.

• 出版日期2013-1-4
• 单位四川大学