Oxyallyl cation promoted dearomative semipinacol rearrangement: a facile stereodivergent synthesis of spiro-indolines with contiguous quaternary centers.
Chem Commun (Camb)
; 57(54): 6632-6635, 2021 Jul 06.
Article
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| MEDLINE
| ID: mdl-34124740
ABSTRACT
A novel oxyallyl cation promoted semipinacol rearrangement of indole-type allylic alcohols was disclosed for the stereodivergent synthesis of spiro-indolines. A variety of spiro-indolines were obtained with moderate to good yields. Three contiguous stereocenters, two of which are vicinal quaternary centers, were effectively formed with good diastereoselectivity. It is worth noting that two diastereoisomers of rearranged products can be readily achieved by easily regulating the reaction conditions. This method may provide an applicable approach for the synthesis of natural indole alkaloids.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Chem Commun (Camb)
Asunto de la revista:
QUIMICA
Año:
2021
Tipo del documento:
Article