Details

Autor(en) / Beteiligte

• Liu, Xiong-Wei
• Chen, Zi-Yue
• Liu, Ren-Ming
• Zhang, Wen-Hui
• Pan, Bo-Wen
• Zhou, Jian
• Tian, You-Ping
• Zhou, Ying
• Liu, Xiong-Li

Titel

Fischer's base-triggered formal (3+2) cycloadditions with 3-isothiocyanato oxindoles as acceptor-donor synthons

Ist Teil von

• Chemical communications (Cambridge, England), 2023-04, Vol.59 (31), p.4652-4655

Ort / Verlag

England: Royal Society of Chemistry

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Herein, previously unreported Fischer's base reactants serving as useful 2C building blocks in (3+2) cycloaddition reactions to build a library of bispiro[Fischer's base-oxindole] hybrids are described. These structurally intriguing products containing three adjacent quaternary stereocentres were smoothly afforded in up to 82% yield and >20 : 1 dr under catalyst-free conditions. Notably, the present protocol firstly employs 3-isothiocyanato oxindole serving as an acceptor and then as a donor in the formal (3+2) cycloadditions, allowing practical, straightforward access to structurally diverse cycloadducts. This work expands the applicability scope of 3-isothiocyanato oxindoles, which have been limited to behaving as donor/acceptor-based synthons in cycloadditions in previous work. Examples of Fischer's base-triggered (3+2) cycloadditions and expanding the applicability scope of 3-isothiocyanato oxindoles.