A novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides

An efficient one-pot three-component procedure for the synthesis of new chiral spiro oxindolopyrrolidines/ pyrrolizidines with highly regio- and diastereo-enantio selective from 1,3-dipolarcycloaddition of azomethine ylides and chiral menthol-drived trans-cinnamic are described. The mechanism of the reaction is discussed on the basis of the assignment of the absolute configurationof one of the cycloaddition products, which was obtained by single crystal X-ray analysis.

Keywords:

Chiral spiro oxindolopyrrolidines , pyrrolizidines , azomethine ylides , chiral mentholdrived trans-cinnamic , isatin , sarcosine