Catalytic hydrative cyclization of aldehyde-ynamides with water for synthesis of medium-sized lactams

被引：20
作者：
Zhu, Bo-Han [1 ]
Zheng, Yan-Xin [1 ]
Kang, Wei [1 ]
Deng, Chao [2 ,3 ]
Zhou, Jin-Mei [1 ]
Ye, Long-Wu [1 ,4 ]
机构：
[1] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China
[2] Nanjing Agr Univ, Coll Sci, Jiangsu Key Lab Pesticide Sci, Nanjing 210095, Peoples R China
[3] Nanjing Agr Univ, Coll Sci, Dept Chem, Nanjing 210095, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
SCIENCE CHINA-CHEMISTRY | 2021年 / 64卷 / 11期
基金：
中国国家自然科学基金;
关键词：
ynamides; cyclization; lactams; diastereoselectivity; N-heterocycles; EFFICIENT SYNTHESIS; TETHERED YNAMIDE; ALDOL REACTIONS; RAPID ACCESS; REGIOSELECTIVITY; CYCLOADDITION; CARBONYLATION; DERIVATIVES; LACTONES; SEQUENCE;
D O I：
10.1007/s11426-021-1069-7
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A non-noble metal catalyzed hydrative cyclization of aldehyde-ynamides for efficient and practical synthesis of medium-sized lactams (7- to 9-membered rings) is disclosed. Compared with previous hydrative cyclization for the formation of six-membered lactams (cis-form), a totally inverse diastereoselectivity (trans-form) of medium-sized lactams is observed. In addition, this protocol delivers valuable medium-sized lactams in moderate to good yields with high diastereoselectivities. Moreover, a rational mechanism to understand this inversion of diastereoselectivity is proposed based on theoretical calculations.
引用
收藏
页码：1985 / 1989
页数：5
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