Reduction of 2-Alkyl-2-carbomethoxy-cyclopentanone Derivatives with Sodium Borohydride. II. The Elucidation of the Diastereoselective Control^a

^aThis work represents the contribution # 19 from LASSBio, UFRJ.

Abstract

The synthesis and reduction of four new 2-substituted β-keto-ester derivatives (6–9), employing inexpensive sodium borohydride, were achieved to evaluate the diastereoselectivity of the reduction process of 2-allyl-2-carbomethoxy cyclopentanone derivative (1a) in the same conditions. These results indicating that the diastereoselective control in this process depend on blockage of the re-face of (1a) by a proposed carbonyl-π-stacking type interaction.

^aThis work represents the contribution # 19 from LASSBio, UFRJ.

Notes

^aThis work represents the contribution # 19 from LASSBio, UFRJ.