Copper-Catalyzed Asymmetric Synthesis of Bicyclo[3.n.1]alkenones

被引：2

作者：

Liao, Zhehui ^{[1
]}

Zhang, Jiantao ^{[2
]}

Cao, Tongxiang ^{[1
]}

Zhu, Shifa ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Peoples R China

[2] Guangdong Univ Petrochem Technol, Coll Chem, Maoming 525000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 07期

基金：

中国博士后科学基金;

关键词：

ALPHA-ARYLATIVE DESYMMETRIZATION; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; CONSTRUCTION; CYCLIZATION;

D O I：

10.1021/acs.joc.1c00146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of highly strained bicyclo[3.n.1]alkenones have been successfully constructed in good-to-excellent enantioselectivities and moderate-to-good yields via copper-catalyzed formal [3+3] cycloaddition. The versatile chiral cycloadducts could be selectively converted into various valuable bridge systems, which hold considerable potential for the construction of natural and bioactive compounds containing a [3.n.1] moiety.

引用

页码：5388 / 5400

页数：13

共 50 条

[1] Acid-Catalyzed Synthesis of Bicyclo[3.n.1]alkenediones
Michaelides, Iacovos N.
Darses, Benjamin
Dixon, Darren J.
[J]. ORGANIC LETTERS, 2011, 13 (04) : 664 - 667
[2] Desymmetrization of Bicyclo[3.n.1]-3-one Derivatives by Palladium-Catalyzed Asymmetric Allylic Alkylation
Yu, Yang
Yang, Xiao-Fei
Xu, Chao-Fan
Ding, Chang-Hua
Hou, Xue-Long
[J]. ORGANIC LETTERS, 2013, 15 (15) : 3880 - 3883
[3] Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations
Burns, Alan R.
Madec, Amael G. E.
Low, Darryl W.
Roy, Iain D.
Lam, Hon Wai
[J]. CHEMICAL SCIENCE, 2015, 6 (06) : 3550 - 3555
[4] Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization
Itagaki, N
Kimura, M
Sugahara, T
Iwabuchi, Y
[J]. ORGANIC LETTERS, 2005, 7 (19) : 4185 - 4188
[5] β,β′- and α,β,β′-annulation reactions of cyclic enamines:: Enantioselective synthesis of bicyclo[3.n.1]alkenones (n=2, 3) and tricyclo[3.3.0.02,8]octanes from Fischer alkenyl carbene complexes
Barluenga, J
Ballesteros, A
Santamaría, J
de la Rúa, RB
Rubio, E
Tomás, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12874 - 12875
[6] Asymmetric Synthesis of γ-Amino Alcohols by Copper-Catalyzed Hydroamination
Ichikawa, Saki
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2019, 21 (21) : 8736 - 8739
[7] Stereoselective synthesis of bicyclo[3.n.1]alkenone frameworks by Lewis acid-catalysis
Pathipati, Stalin R.
Eriksson, Lars
Selander, Nicklas
[J]. CHEMICAL COMMUNICATIONS, 2017, 53 (82) : 11353 - 11356
[8] Synergistic Catalysis: Metal/Proton-Catalyzed Cyclization of Alkynones Toward Bicyclo[3.n.1]alkanones
Zhu, Shifa
Zhang, Qiaohui
Chen, Kai
Jiang, Huanfeng
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (32) : 9414 - 9418
[9] Copper-Catalyzed Asymmetric 1,4-Hydroboration of Coumarins with Pinacolborane: Asymmetric Synthesis of Dihydrocoumarins
Kim, Hyohyun
Yun, Jaesook
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (11-12) : 1881 - 1885
[10] Asymmetric Synthesis of SCF3-Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes
Kojima, Yuki
Nishii, Yuji
Hirano, Koji
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (24)

← 1 2 3 4 5 →