[3+2]-cycloaddition reactions of thioisatin with L-proline and (R)-(-)-thiaproline

摘要

The[3+2]-cycloaddition reactions of cyclic secondary alpha-amino acids viz L-proline and (R)-(-)-thiaproline with 5-methylthioisatin. via azomethine ylide in the presence of dipolarophiles afford azabicyclooctane derivatives in moderate-to-good yields. The cycloadducts have been characterized by elemental analysis and spectral techniques viz IR, H-1 NMR, C-13 NMR, MASS. In. addition, stereochemical aspects of the cycloaddition have been ascertained by MOPAC-6 calculations using AM1 hamiltonians.