Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon

An asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes has been developed via Si-to-C chirality transfer. Mechanistic studies reveal that the silyl group migrates with retention of configuration. The stereochemical outcome of the newly formed stereogenic carbon center, which has re...

Descripción completa

Detalles Bibliográficos
Autores principales: Wu, Ya, Chen, Hua, Yang, Wenyu, Fan, Yu, Gao, Lu, Su, Zhishan, Hu, Changwei, Song, Zhenlei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070365/
https://www.ncbi.nlm.nih.gov/pubmed/35530994
http://dx.doi.org/10.1039/c9ra05482k
Descripción
Sumario:An asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes has been developed via Si-to-C chirality transfer. Mechanistic studies reveal that the silyl group migrates with retention of configuration. The stereochemical outcome of the newly formed stereogenic carbon center, which has remained a longstanding question, is also clarified, suggesting a diastereoselective Si to C chirality transfer without loss of enantiomeric excess.

Ejemplares similares