Asymmetric retro-[1, 4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon. Issue 45 (21st August 2019)

• Record Type: Journal Article
• Authors: Wu, Ya; Chen, Hua; Yang, Wenyu; Fan, Yu; Gao, Lu; Su, Zhishan; Hu, Changwei; Song, Zhenlei
• Is Part Of: RSC advances. Volume 9:Issue 45(2019)
• Page Start: 26209
• Page End: 26213
• Publication Date: 2019-08-21
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9ra05482k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Asymmetric retro-[1, 4]-Brook rearrangement of 3-silyl allyloxysilanes has been developed involving Si-to-C chirality transfer, which is diastereoselective without loss of enantiomeric excess. Abstract : 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.