Highly Enantioselective Construction of Multifunctional Silicon‐Stereogenic Silacycles by Asymmetric Enamine Catalysis

We report the first highly enantioselective construction of silicon‐stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular aldolization of prochiral siladials was thus developed for the facile access of multifunctional silicon‐stereogenic silacycles in high to exc...

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Published inAngewandte Chemie International Edition Vol. 62; no. 9; pp. e202217724 - n/a
Main Authors Zhang, Xue‐Xin, Gao, Yang, Zhang, Yan‐Xue, Zhou, Jian, Yu, Jin‐Sheng
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 20.02.2023
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Adducts
Asymmetric Enamine Catalysis
Asymmetry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Desymmetric Adolization
Enantiomers
Fluoroalkyl
Physical Sciences
Science & Technology
Silacycles
Silicon
Silicon compounds
Silicon-Stereocenter
ORGANIC CATALYSIS
ORGANOCATALYSIS
DESYMMETRIZATION
STRATEGIES
MOLECULES
Fluoroalkyl
AMINO-ACID
Desymmetric Adolization
Silicon-Stereocenter
CHEMISTRY
FLUORINE
Asymmetric Enamine Catalysis
Silacycles
DERIVATIVES
DIRECT ALDOL REACTIONS
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Abstract We report the first highly enantioselective construction of silicon‐stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular aldolization of prochiral siladials was thus developed for the facile access of multifunctional silicon‐stereogenic silacycles in high to excellent enantioselectivity. With an enal moiety, these adducts could be readily elaborated for the diverse synthesis of silicon‐stereogenic compounds, and for late‐stage modification. The enantioselective construction of silicon‐stereocenter by asymmetric enamine catalysis is reported. The reaction proceeds via an unprecedented desymmetric intramolecular aldolization of prochiral siladials for the diverse synthesis of multifunctional silicon‐stereogenic silacycles.
AbstractList We report the first highly enantioselective construction of silicon-stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular aldolization of prochiral siladials was thus developed for the facile access of multifunctional silicon-stereogenic silacycles in high to excellent enantioselectivity. With an enal moiety, these adducts could be readily elaborated for the diverse synthesis of silicon-stereogenic compounds, and for late-stage modification.
Abstract We report the first highly enantioselective construction of silicon‐stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular aldolization of prochiral siladials was thus developed for the facile access of multifunctional silicon‐stereogenic silacycles in high to excellent enantioselectivity. With an enal moiety, these adducts could be readily elaborated for the diverse synthesis of silicon‐stereogenic compounds, and for late‐stage modification.
We report the first highly enantioselective construction of silicon‐stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular aldolization of prochiral siladials was thus developed for the facile access of multifunctional silicon‐stereogenic silacycles in high to excellent enantioselectivity. With an enal moiety, these adducts could be readily elaborated for the diverse synthesis of silicon‐stereogenic compounds, and for late‐stage modification. The enantioselective construction of silicon‐stereocenter by asymmetric enamine catalysis is reported. The reaction proceeds via an unprecedented desymmetric intramolecular aldolization of prochiral siladials for the diverse synthesis of multifunctional silicon‐stereogenic silacycles.
Author Gao, Yang
Zhou, Jian
Zhang, Xue‐Xin
Zhang, Yan‐Xue
Yu, Jin‐Sheng
Author_xml – sequence: 1
  givenname: Xue‐Xin
  surname: Zhang
  fullname: Zhang, Xue‐Xin
  organization: East China Normal University
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  givenname: Yang
  surname: Gao
  fullname: Gao, Yang
  organization: East China Normal University
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  givenname: Yan‐Xue
  surname: Zhang
  fullname: Zhang, Yan‐Xue
  organization: East China Normal University
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  givenname: Jian
  surname: Zhou
  fullname: Zhou, Jian
  organization: Hainan Normal University
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  givenname: Jin‐Sheng
  orcidid: 0000-0002-0619-2037
  surname: Yu
  fullname: Yu, Jin‐Sheng
  email: jsyu@chem.ecnu.edu.cn
  organization: Hainan Normal University
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Issue 9
Keywords ORGANIC CATALYSIS
ORGANOCATALYSIS
DESYMMETRIZATION
STRATEGIES
MOLECULES
Fluoroalkyl
AMINO-ACID
Desymmetric Adolization
Silicon-Stereocenter
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Asymmetric Enamine Catalysis
Silacycles
DERIVATIVES
DIRECT ALDOL REACTIONS
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Snippet We report the first highly enantioselective construction of silicon‐stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular...
We report the first highly enantioselective construction of silicon-stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular...
Abstract We report the first highly enantioselective construction of silicon‐stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric...
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StartPage e202217724
SubjectTerms Adducts
Asymmetric Enamine Catalysis
Asymmetry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Desymmetric Adolization
Enantiomers
Fluoroalkyl
Physical Sciences
Science & Technology
Silacycles
Silicon
Silicon compounds
Silicon-Stereocenter
Title Highly Enantioselective Construction of Multifunctional Silicon‐Stereogenic Silacycles by Asymmetric Enamine Catalysis
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202217724
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000919872400001
https://www.ncbi.nlm.nih.gov/pubmed/36625565
https://www.proquest.com/docview/2777148629/abstract/
https://search.proquest.com/docview/2763332918
Volume 62
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