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

页码：1985 / 1989

页数：5

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