Mild arylboronic acid catalyzed selective [4 + 3] cycloadditions: access to cyclohepta[b]benzofurans and cyclohepta[b]indoles

2015 ◽  
Vol 13 (23) ◽  
pp. 6449-6452 ◽  
Author(s):  
Kou-Sen Cao ◽  
Hong-Xu Bian ◽  
Wen-Hua Zheng
Keyword(s):  
Cycloaddition Reaction ◽  
Arylboronic Acid ◽  
Acid Catalyzed

The first example of arylboronic acid catalyzed [4 + 3] cycloaddition reaction is reported.

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes

2019 ◽  
Author(s):  
Juha Siitonen ◽  
Padmanabha V. Kattamuri ◽  
Muhammed Yousufuddin ◽  
Laszlo Kurti
Keyword(s):  
Total Synthesis ◽  
Acid Catalysts ◽  
Mechanistic Studies ◽  
Arylboronic Acid ◽  
Synthetic Utility ◽  
Acid Catalyzed

Unprotected keto- and aldoximes are readily <i>C</i>-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted <i>N</i>-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid <i>N</i>-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.<br>

Synthesis of 4-heterocyclyl-hexahydro-8-methoxyfuro[3,2-c]quinolines by Lewis acid catalyzed [4 + 2]cycloaddition reaction

1986 ◽  
Vol 23 (1) ◽  
pp. 185-187 ◽  
Author(s):  
Tetsuji Kametani ◽  
Hiroko Furuyama ◽  
Yukari Fukuoka ◽  
Hajime Takeda ◽  
Yukio Suzuki ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Cycloaddition Reaction ◽  
Acid Catalyzed

Synthetic Studies towards the Total Synthesis of Indole Alkaloids Containing Indolyl Lactam Frameworks

Synlett ◽  
2020 ◽  
Author(s):  
Fu-She Han ◽  
Dong-Xing Tan
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Cycloaddition Reaction ◽  
Terminal Olefin ◽  
Asymmetric Reaction ◽  
Rapid Construction ◽  
Fused Ring ◽  
Acid Catalyzed ◽  
Synthetic Studies ◽  
Type Substitution

AbstractIn this account, recent progress on the synthetic studies of several monoterpene indole alkaloids, (±)-mersicarpine, misassigned (±)-tronoharine, and (±)-leuconodines D and E, is summarized. Specifically, the rationale for the design and development of the Lewis acid catalyzed SN1-type substitution and formal [3+3] cycloaddition reaction of indol-2-yl carbinols, and the Pd-catalyzed aerobic oxidative intramolecular Heck cross-coupling of indolyl amides tethered with a terminal olefin functionality, are emphasized. These key reactions set the basis for the rapid construction of the fused ring skeleton containing an all-carbon quaternary center at the indol-2-yl position.1 Introduction2 Synthetic Study of (±)-Mersicarpine3 Synthetic Study of the Misassigned (±)-Tronoharine4 Study of the Asymmetric Reaction of Indol-2-yl Carbinols5 Synthetic Study of (±)-Leuconodines D and E6 Conclusion

Application of the Lewis Acid Catalyzed [4+2]Cycloaddition Reaction to Synthesis of Natural Quinoline Alkaloids

Heterocycles ◽  
1986 ◽  
Vol 24 (12) ◽  
pp. 3385 ◽  
Author(s):  
Tetsuji Kametani ◽  
Hajime Takeda ◽  
Yukio Suzuki ◽  
Hiroko Kasai ◽  
Toshio Honda
Keyword(s):  
Lewis Acid ◽  
Cycloaddition Reaction ◽  
Quinoline Alkaloids ◽  
Acid Catalyzed

Mechanism of arylboronic acid-catalyzed amidation reaction between carboxylic acids and amines

2013 ◽  
Vol 11 (13) ◽  
pp. 2140 ◽  
Author(s):  
Chen Wang ◽  
Hai-Zhu Yu ◽  
Yao Fu ◽  
Qing-Xiang Guo
Keyword(s):  
Carboxylic Acids ◽  
Arylboronic Acid ◽  
Amidation Reaction ◽  
Acid Catalyzed

ChemInform Abstract: Chiral Phosphoric Acid Catalyzed Enantioselective 1,3-Dipolar Cycloaddition Reaction of Azlactones.

ChemInform ◽  
2016 ◽  
Vol 47 (21) ◽  
Author(s):  
Zhenhua Zhang ◽  
Wangsheng Sun ◽  
Gongming Zhu ◽  
Junxian Yang ◽  
Ming Zhang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed
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