A Mechanistic Switch from Homoallylation to Cyclopropylcarbinylation of Aldehydes.
Org Lett
; 24(25): 4660-4664, 2022 07 01.
Article
en En
| MEDLINE
| ID: mdl-35735239
ABSTRACT
Cyclopropanated allylboration reagents participate in homoallylation reactions of aliphatic and aromatic aldehydes, generating allylic-substituted alkenes that are difficult to produce via other methods. In studying the effect of cyclopropane substituents, we discovered that an aryl substituent completely changes the outcome to cyclopropylcarbinylation, as if the cyclopropylcarbinyl fragment were transferred intact. However, density functional theory computation suggested a novel mechanism involving ring opening and reclosure, which is supported by experimental evidence.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Aldehídos
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Alquenos
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2022
Tipo del documento:
Article
País de afiliación:
Estados Unidos