标题：Novel Small Organic Molecules for a Highly Enantioselective Direct Aldol Reaction
来源：《美国化学会志》2003年125卷第18期，5262-5263页
作者：中科院成都有机化学研究所 Xin Cui（崔欣）, Liu-Zhu Gong（龚流柱）, Ai-Qiao Mi（宓爱巧）, Yao-Zhong Jiang（蒋耀忠）
中科院成都有机化学研究所、四川大学化学工程学院 Zhuo Tang（唐卓）
四川大学化学工程学院 Luo-Ting Yu
北京大学化学与分子工程学院 国家分子动力学与稳态结构重点实验室 Fan Jiang（蒋帆）, Yun-Dong Wu（吴云东）
Research Fronts: ENANTIOSELECTIVE DIRECT ALDOL REACTIONS CATALYZED; HIGHLY ENANTIOSELECTIVE DIRECT ALDOL REACTION; DIRECT ASYMMETRIC ALDOL REACTION; N-TERMINAL PROLYL-PEPTIDES EFFICIENTLY CATALYZE ENANTIOSELECTIVE ALDOL; ASYMMETRIC AMINOCATALYSIS
领域：化学
摘要：Novel organic molecules containing an L-proline amide moiety and a terminal hydroxyl for catalyzing direct asymmetric aldol reactions of aldehydes in neat acetone are designed and prepared. Catalyst 3d, prepared from L-proline and (1S,2S)-diphenyl-2-aminoethanol, exhibits high enantioselectivities of up to 93% ee for aromatic aldehydes and up to >99% ee for aliphatic aldehydes. A theoretical study of transition structures demonstrates the important role of the terminal hydroxyl group in the catalyst in the stereodiscrimination. Our results suggest a new strategy in the design of new organic catalysts for direct asymmetric aldol reactions and related transformations because plentiful chiral resources containing multi-hydrogen bond donors, for example, peptides, might be adopted in the design.
