Stereodivergent and Stereoselective Synthesis of cis- and trans-4-Substituted Prolinols

Abstract

Stereoselective synthesis of 4-substituted prolinol derivatives has been developed. Thus, Suzuki-Miyaura cross-coupling of vinyl triflate provided the common synthetic intermediates toward the stereodivergent synthesis of cisand trans-4-substituted prolinols. These two kinds of target compounds were obtained by diastereoselective hydrogenation of the coupling products with Pd/C and Crabtree catalyst, respectively. In addition, the obtained 4-substituted prolinol was transformed to the corresponding proline derivative via oxidation in one step.