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 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 remain...

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Published inRSC advances Vol. 9; no. 45; pp. 26209 - 26213
Main Authors Wu, Ya, Chen, Hua, Yang, Wenyu, Fan, Yu, Gao, Lu, Su, Zhishan, Hu, Changwei, Song, Zhenlei
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 2019
The Royal Society of Chemistry
Subjects
Carbon
Chemistry
Chirality
Crystallography
Silicon
Stereoselectivity
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Summary:An asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes has been developed 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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ISSN:2046-2069
2046-2069
DOI:10.1039/c9ra05482k