Isatogenols as Precursors for the Synthesis of Fully Substituted Indolines through Regio- and Stereoselective [3 + 2] Cycloaddition Using Various Olefins DOI

Nanaka Ishihara,

Shinji Harada, Masaya Nakajima

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 2908 - 2912

Published: April 1, 2024

Here, we describe a unique reactivity of isatogen derivatives bearing hydroxy group at the C3-position (isatogenol) and their synthetic application to highly regio- stereoselective [3 + 2] cycloaddition reactions. This method provides facile access polyfused functionalized heterocycles including consecutive stereocenters. Furthermore, DFT calculations revealed that hydrogen bonding is key controlling stereoselectivity in using acrylates.

Language: Английский

Regio- and Stereoselective [3 + 2] cycloaddition of Isatogens with functionalized alkenes and its application to the synthesis of Halichrome a DOI

Nanaka Ishihara,

Reiko Fukuoka,

Shinji Harada

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155626 - 155626

Published: April 1, 2025

Language: Английский

Citations

0

Boron Compounds as Key Drivers of Innovation: Exploring Their Role in Environmental Remediation, Sustainable Agriculture, Advanced Biomedical Applications, and Green Chemistry DOI
Metin Yıldırım, Mehmet Erşatır, Mohammed Saleh

et al.

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: 1035, P. 123688 - 123688

Published: April 28, 2025

Language: Английский

Citations

0

Isatogenols as Precursors for the Synthesis of Fully Substituted Indolines through Regio- and Stereoselective [3 + 2] Cycloaddition Using Various Olefins DOI

Nanaka Ishihara,

Shinji Harada, Masaya Nakajima

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 2908 - 2912

Published: April 1, 2024

Here, we describe a unique reactivity of isatogen derivatives bearing hydroxy group at the C3-position (isatogenol) and their synthetic application to highly regio- stereoselective [3 + 2] cycloaddition reactions. This method provides facile access polyfused functionalized heterocycles including consecutive stereocenters. Furthermore, DFT calculations revealed that hydrogen bonding is key controlling stereoselectivity in using acrylates.

Language: Английский

Citations

1