Highly diastereo- and enantioselective organocatalytic addition of acetone to beta-substituted alpha-ketoesters via dynamic kinetic resolution.
L-proline catalyzes the aldol addition reaction of acetone to beta-substituted alpha-ketoesters with dynamic kinetic resolution, providing the desired adduct in good yield with excellent diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to 98% ee). The absolute configuration of the chiral adduct was assigned by single-crystal X-ray diffraction analysis. A tentative explanation of the stereochemical outcome is proposed.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Suzhou, 215123, China.
Jin
J
Yang
Ting
T
Wang
Zhenhua
Z
Ding
Zongxuan
Z
Shen
Yawen
Y
Zhang