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

共 50 条

[41] HYPERVALENT ORGANOIODINE REAGENTS IN THE TRANS-ANNULAR FUNCTIONALIZATION OF MEDIUM-SIZED LACTAMS - SYNTHESIS OF 1-AZABICYCLO COMPOUNDS
DORTA, RL
FRANCISCO, CG
SUAREZ, E
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (16) : 1168 - 1169
[42] Steric-switched defluorofunctionalization selectivity: controlled synthesis of monofluoroalkene-masked medium-sized heterocyclic lactams and lactones
Hao Zeng
Hengyuan Li
Huanfeng Jiang
Chuanle Zhu
Science China Chemistry, 2022, 65 : 554 - 562
[43] Photoinduced sulfonylation cyclization to medium-sized benzo[b]azocine and mechanistic insight
Zhao, Dongyang
Sun, Kai
Tian, Miao
Yan, Bingfei
Li, Wenzuo
Sun, Qing
Zheng, Guangfan
Zhang, Qian
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (13) : 3313 - 3320
[44] Steric-switched defluorofunctionalization selectivity: controlled synthesis of monofluoroalkene-masked medium-sized heterocyclic lactams and lactones
Hao Zeng
Hengyuan Li
Huanfeng Jiang
Chuanle Zhu
Science China(Chemistry), 2022, 65 (03) : 554 - 562
[45] Steric-switched defluorofunctionalization selectivity: controlled synthesis of monofluoroalkene-masked medium-sized heterocyclic lactams and lactones
Zeng, Hao
Li, Hengyuan
Jiang, Huanfeng
Zhu, Chuanle
SCIENCE CHINA-CHEMISTRY, 2022, 65 (03) : 554 - 562
[46] Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings
Jan Otevrel
Macarena Eugui
Sebastijan Ričko
Karl Anker Jørgensen
Nature Synthesis, 2023, 2 : 1142 - 1158
[47] Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings
Otevrel, Jan
Eugui, Macarena
Ricko, Sebastijan
Jorgensen, Karl Anker
NATURE SYNTHESIS, 2023, 2 (12): : 1142 - 1158
[48] Microwave-assisted synthesis of medium-sized heterocycles
Sharma, Abhishek
Appukkuttan, Prasad
van der Eycken, Erik
CHEMICAL COMMUNICATIONS, 2012, 48 (11) : 1623 - 1637
[49] Steric-switched defluorofunctionalization selectivity: controlled synthesis of monofluoroalkene-masked medium-sized heterocyclic lactams and lactones
Hao Zeng
Hengyuan Li
Huanfeng Jiang
Chuanle Zhu
Science China(Chemistry), 2022, (03) : 554 - 562
[50] SYNTHESIS AND PROPERTIES OF MEDIUM-SIZED NONCONJUGATED CARBOCYCLIC ENEDIYNES
GLEITER, R
MERGER, R
TETRAHEDRON LETTERS, 1989, 30 (51) : 7183 - 7186

← 1 2 3 4 5 →