Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides

Two complementary approaches to substituted pyrrolidines via stereocontroll ed 1,3-dipolar cycloaddition reactions of chiral azomethine ylides are desc ribed. In one approach, chiral azomethine ylides were generated by thermoly sis of aziridine carboxylate sultams and trapped with a variety of dipolaro philes to give good yields of the corresponding cycloadducts. In the second approach, chiral azomethine ylides were generated from glycyl sultams by ' imine tautomerization' and trapped with dipolarophiles to give good yields of the corresponding cycloadducts, (C) 2000 Elsevier Science Ltd. All right s reserved.