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...

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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
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author Wu, Ya
Chen, Hua
Yang, Wenyu
Fan, Yu
Gao, Lu
Su, Zhishan
Hu, Changwei
Song, Zhenlei
author_facet Wu, Ya
Chen, Hua
Yang, Wenyu
Fan, Yu
Gao, Lu
Su, Zhishan
Hu, Changwei
Song, Zhenlei
author_sort Wu, Ya
collection PubMed
description 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.
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spelling pubmed-90703652022-05-05 Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon Wu, Ya Chen, Hua Yang, Wenyu Fan, Yu Gao, Lu Su, Zhishan Hu, Changwei Song, Zhenlei RSC Adv Chemistry 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. The Royal Society of Chemistry 2019-08-21 /pmc/articles/PMC9070365/ /pubmed/35530994 http://dx.doi.org/10.1039/c9ra05482k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Wu, Ya
Chen, Hua
Yang, Wenyu
Fan, Yu
Gao, Lu
Su, Zhishan
Hu, Changwei
Song, Zhenlei
Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon
title Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon
title_full Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon
title_fullStr Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon
title_full_unstemmed Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon
title_short Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon
title_sort asymmetric retro-[1,4]-brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070365/
https://www.ncbi.nlm.nih.gov/pubmed/35530994
http://dx.doi.org/10.1039/c9ra05482k
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