Stereoconvergent Approach to the Enantioselective Construction of α‐Quaternary Alcohols by Radical Epoxide Allylation

We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α‐quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)‐promoted i...

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Published inAngewandte Chemie International Edition Vol. 63; no. 29; pp. e202405911 - n/a
Main Authors Höthker, Sebastian, Plato, Annika, Grimme, Stefan, Qu, Zheng‐Wang, Gansäuer, Andreas
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 15.07.2024
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alcohols
Alkenes
Allyl compounds
allylation
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
convergence
Enantiomers
Epoxidation
Epoxides
Intermediates
Isomerization
Physical Sciences
radicals
Science & Technology
titanium
CATALYSIS
radicals
convergence
titanium
C-H FUNCTIONALIZATION
epoxidation
REDUCTION
STEREOCENTERS
ASYMMETRIC EPOXIDATION
BASIS-SETS
STEREOGENIC CENTERS
BETA-HYDROXY KETONES
allylation
DERIVATIVES
CONJUGATE ADDITION
Online AccessGet full text

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Abstract We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α‐quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)‐promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all‐carbon quaternary stereocenters in a unique fashion. We demonstrate an operationally simple approach towards α‐quaternary alcohols in good to excellent diastereomeric and enantiomeric ratios in two steps from diastereomeric mixtures of trisubstituted olefins. Our method relies on an unprecedented, radical, intramolecular syn‐allyl transfer to intermediate β‐titanoxy radicals resulting from an Cp2TiIIIallyl‐induced fragmentation of epoxide precursors.
AbstractList We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α-quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)-promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all-carbon quaternary stereocenters in a unique fashion.We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α-quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)-promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all-carbon quaternary stereocenters in a unique fashion.
We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched alpha-quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)-promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all-carbon quaternary stereocenters in a unique fashion.
We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α‐quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)‐promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all‐carbon quaternary stereocenters in a unique fashion.
We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α‐quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)‐promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all‐carbon quaternary stereocenters in a unique fashion. We demonstrate an operationally simple approach towards α‐quaternary alcohols in good to excellent diastereomeric and enantiomeric ratios in two steps from diastereomeric mixtures of trisubstituted olefins. Our method relies on an unprecedented, radical, intramolecular syn‐allyl transfer to intermediate β‐titanoxy radicals resulting from an Cp2TiIIIallyl‐induced fragmentation of epoxide precursors.
We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α ‐quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)‐promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all‐carbon quaternary stereocenters in a unique fashion.
ArticleNumber 202405911
Author Plato, Annika
Höthker, Sebastian
Qu, Zheng‐Wang
Gansäuer, Andreas
Grimme, Stefan
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  givenname: Annika
  surname: Plato
  fullname: Plato, Annika
  organization: Universität Bonn
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  givenname: Stefan
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  surname: Grimme
  fullname: Grimme, Stefan
  organization: Universität Bonn
– sequence: 4
  givenname: Zheng‐Wang
  orcidid: 0000-0001-6631-3681
  surname: Qu
  fullname: Qu, Zheng‐Wang
  email: qu@thch.uni-bonn.de
  organization: Universität Bonn
– sequence: 5
  givenname: Andreas
  orcidid: 0000-0003-2622-6369
  surname: Gansäuer
  fullname: Gansäuer, Andreas
  email: andreas.gansaeuer@uni-bonn.de
  organization: Universität Bonn
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CitedBy_id crossref_primary_10_1002_chem_202403624
crossref_primary_10_1002_cctc_202400829
crossref_primary_10_1055_a_2457_0045
crossref_primary_10_3390_molecules29184350
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Issue 29
Keywords CATALYSIS
radicals
convergence
titanium
C-H FUNCTIONALIZATION
epoxidation
REDUCTION
STEREOCENTERS
ASYMMETRIC EPOXIDATION
BASIS-SETS
STEREOGENIC CENTERS
BETA-HYDROXY KETONES
allylation
DERIVATIVES
CONJUGATE ADDITION
Language English
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Snippet We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α‐quaternary alcohols in two steps...
We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α ‐quaternary alcohols in two steps...
We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched alpha-quaternary alcohols in two...
We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α-quaternary alcohols in two steps...
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StartPage e202405911
SubjectTerms Alcohols
Alkenes
Allyl compounds
allylation
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
convergence
Enantiomers
Epoxidation
Epoxides
Intermediates
Isomerization
Physical Sciences
radicals
Science & Technology
titanium
Title Stereoconvergent Approach to the Enantioselective Construction of α‐Quaternary Alcohols by Radical Epoxide Allylation
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202405911
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001265568500074
https://www.ncbi.nlm.nih.gov/pubmed/38669602
https://www.proquest.com/docview/3076685455
https://www.proquest.com/docview/3047952840
Volume 63
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