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  The Silicon–Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones

Zhou, H., Zhang, P., & List, B. (2021). The Silicon–Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones. Synlett, 32(19), 1953-1956. doi:10.1055/a-1670-5829.

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Zhou-Zhang-List.pdf (Publisher version), 377KB
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 Creators:
Zhou, Hui1, Author           
Zhang, Pinglu1, 2, Author           
List, Benjamin1, Author           
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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, Zhejiang, P. R. China, ou_persistent22              

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Free keywords: asymmetric catalysis; organocatalysis; enol silanes
 Abstract: We have recently reported the strong and confined, chiral acid-catalyzed asymmetric ‘silicon−hydrogen exchange reaction’. One aspect of this transformation is that it enables access to enantiopure enol silanes in a tautomerizing σ-bond metathesis, via deprotosilylation of ketones with allyl silanes as the silicon source. However, until today, this reaction has not been applied to racemic, 2-substituted, cyclic ketones. We show here that these important substrates readily undergo a highly enantioselective kinetic resolution furnishing the corresponding kinetically preferred enol silanes. Mechanistic studies suggest the fascinating possibility of advancing the process to a dynamic kinetic resolution.

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Language(s): eng - English
 Dates: 2021-09-172021-10-142021-10-152021-12-01
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1055/a-1670-5829
 Degree: -

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Title: Synlett
  Abbreviation : Synlett
Source Genre: Journal
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Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: - Volume / Issue: 32 (19) Sequence Number: - Start / End Page: 1953 - 1956 Identifier: ISSN: 0936-5214
CoNE: https://pure.mpg.de/cone/journals/resource/954925570856