An efficient, one-pot, three-component procedure for the synthesis of chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition

作者：Salahi Farbod; Taghizadeh Mohammad Javad; Arvinnezhad Hamid; Moemeni Mehdi; Jadidi Khosrow^*; Notash Behrouz

来源：Tetrahedron Letters, 2014, 55(9): 1515-1518.

DOI：10.1016/j.tetlet.2013.11.097

• Catalytic asymmetric multicomponent
• reaction
• Asymmetric 1,3-dipolar cycloaddition
• Cyclohexane-1,2-bis(arylmethyleneamine)
• Azomethine ylide
• Chiral spirooxindolopyrrolizidines

The catalytic, highly regio-, diastereo-, and enantioselective synthesis of a small library of chiral spirooxindolopyrrolizidines via a three-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophiles, 3-(2-alkenoy1)-1,3-oxazolidin-2-ones, is described. A chiral copper(II) complex of cyclohexane-1,2-bis(arylmethyleneamine) catalyzed this process at room temperature. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts.

• 出版日期2014-2-26