铜催化环酮亚胺与β,γ-不饱和N-酰基吡唑不对称Mannich-Type反应
收稿日期: 2022-09-28
修回日期: 2022-11-14
网络出版日期: 2022-12-12
基金资助
中国科学院青年创新促进会(2022375); 国家自然科学基金(21871251); 国家自然科学基金(22171258); 中国科学院生物资源(KFJ-BRP-008)
Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles
Received date: 2022-09-28
Revised date: 2022-11-14
Online published: 2022-12-12
Supported by
Youth Innovation Promotion Association of Chinese Academy of Sciences(2022375); National Natural Science Foundation of China(21871251); National Natural Science Foundation of China(22171258); Biological Resources Program, Chinese Academy of Sciences(KFJ-BRP-008)
手性苯并环状磺酰胺是一类重要的生物活性化合物和功能性有机分子, 发展其高效的不对称催化合成方法一直备受关注. 铜催化环状N-磺酰亚胺与β,γ-不饱和N-酰基吡唑的不对称Mannich-type反应是一类新合成策略. 在温和反应条件下, 该方法以良好的产率, 优异的选择性(区域选择性(γ/α>20/1)、非对映选择性(dr>20/1)、对映选择性(up to 93% ee)得到γ-加成产物手性苯并五元环状磺酰胺, 且底物范围较广, 官能团兼容性较好, 为结构多样的手性苯并环状磺酰胺及其衍生物合成提供新的合成途径.
关键词： 铜催化; 手性苯并环状磺酰胺; 不对称Mannich反应; γ-加成产物
刘洋 , 黄翔 , 王敏 , 廖建 . 铜催化环酮亚胺与β,γ-不饱和N-酰基吡唑不对称Mannich-Type反应[J]. 有机化学, 2023 , 43(4) : 1499 -1509 . DOI: 10.6023/cjoc202209034
Chiral benzosultams are an important category of bioactive compounds and functional organic molecules. Therefore, great efforts have been devoted for developing efficient methods for their preparation. A copper-catalyzed direct asymmetric Mannich-type reaction of cyclic N-sulfonyl α-iminoesters with β,γ-unsaturated N-acylpyrazoles was developed. Under mild conditions, γ-adducts were delivered in good yields with excellent regio- (γ/α>20/1), diastereoselectivities (dr>20/1) and high enantioselectivities (up to 93% ee). This method, with wide substrate-scopes and good functional group compatibility, provides potentiality for the synthesis of structurally diverse chiral benzosultam derivatives.
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