脯氨酸二肽催化的不对称直接Aldol反应

Direct Asymmetric Aldol Reaction Catalyzed by Proline-Proline Dipeptide

以(S)-脯氨酸和(R)-脯氨酸为原料合成了二肽H-(S)-Pro-(S)-Pro-OH(1)和H-(S)-Pro(-R)-Pro-OH(2),分别以两种二肽催化了不对称直接A ldol反应,获得了相同立体构型(S)的产物,与(S)-脯氨酸催化所得的产物构型(R)相反.该催化剂的立体选择性不高(ee<21%).理论计算的结果与实验结果吻合.

Two dipeptides, H-（S）-Pro-（S）-Pro-OH （1） and H-（S）-Pro-（R）-Pro-OH （2）, were prepared from （S）- and （R）-proline, and applied in direct asymmetric Aldol reaction. In both cases, the product had （S）- configuration, which was opposite to that obtained by （S）-proline catalysis. Low enantioselectivities （less than 21%） were found. Data from the computational research could well explain the experimental results.