Journal
ORGANIC LETTERS
Volume 24, Issue 24, Pages 4389-4393Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01607
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Funding
- JSPS KAKENHI [18K05103, 19H03350]
- MEXT KAKENHI [JP21H05211]
- AMED Platform for Supporting Drug Discovery and Life Science Research [jp19am0101092j0003]
- BINDS from AMED [22ama121042j0001, 22ama121034j0001]
- Takeda Science Foundation
- Grants-in-Aid for Scientific Research [19H03350, 18K05103] Funding Source: KAKEN
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A Zn(OTf)(2)-catalyzed domino reaction was developed for the synthesis of spirocyclic indolines from enamide-ynamides in the presence of trimethylsilyl cyanide. This reaction involved the cyclization of enamide to ynamide followed by cyanide addition, resulting in the formation of spiroindolopyrrolidines with excellent diastereoselectivity.
The Zn(OTf)(2)-catalyzed domino reaction of enamide-ynamides in the presence of trimethylsilyl cyanide as an external nucleophile to construct spirocyclic indolines was developed. This domino reaction involved cyclization of enamide to ynamide to generate 4',5'-dihydrospiro[indoline-3,3'-pyrrol]-1'-ium followed by cyanide addition to produce spiroindolopyrrolidines with good diastereoselectivity.
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