Redox-neutral α-functionalization of pyrrolidines: facile access to α-aryl-substituted pyrrolidines.
RSC Adv
; 14(17): 11986-11991, 2024 Apr 10.
Article
em En
| MEDLINE
| ID: mdl-38623291
ABSTRACT
α-Aryl-substituted pyrrolidine moiety is found in many natural alkaloids. Starting from pyrrolidine, we were able to synthesize α-aryl-substituted pyrrolidines in one step using quinone monoacetal as the oxidizing agent and DABCO as the base. We also discovered the reaction condition needed to efficiently remove the N-aryl moiety from the α-arylated product. When the above reaction was carried out without the addition of an aryl nucleophile, the reaction of pyrrolidine and quinone monoacetal in 2,2,2-trifluoroethanol afforded octahydro-dipyrroloquinoline in high yield, which has the same skeleton as that of natural product incargranine B.
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01-internacional
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MEDLINE
Idioma:
En
Revista:
RSC Adv
Ano de publicação:
2024
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Article