An Iron/Amine-Catalyzed Cascade Process for the Enantioselective Functionalization of Allylic Alcohols
Three is a lucky number: An enantioselective transformation of allylic alcohols into β‐chiral saturated alcohols has been developed by combining two distinct metal‐ and organocatalyzed catalytic cycles. This waste‐free triple cascade process merges an iron‐catalyzed borrowing‐hydrogen step with an a...
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Published in | Angewandte Chemie International Edition Vol. 52; no. 49; pp. 12883 - 12887 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
02.12.2013
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc Wiley-VCH Verlag |
Edition | International ed. in English |
Subjects | |
Online Access | Get full text |
ISSN | 1433-7851 1521-3773 1521-3773 |
DOI | 10.1002/anie.201307295 |
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Abstract | Three is a lucky number: An enantioselective transformation of allylic alcohols into β‐chiral saturated alcohols has been developed by combining two distinct metal‐ and organocatalyzed catalytic cycles. This waste‐free triple cascade process merges an iron‐catalyzed borrowing‐hydrogen step with an aminocatalyzed nucleophilic addition reaction. |
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AbstractList | Three is a lucky number: An enantioselective transformation of allylic alcohols into β-chiral saturated alcohols has been developed by combining two distinct metal- and organocatalyzed catalytic cycles. This waste-free triple cascade process merges an iron-catalyzed borrowing-hydrogen step with an aminocatalyzed nucleophilic addition reaction.Three is a lucky number: An enantioselective transformation of allylic alcohols into β-chiral saturated alcohols has been developed by combining two distinct metal- and organocatalyzed catalytic cycles. This waste-free triple cascade process merges an iron-catalyzed borrowing-hydrogen step with an aminocatalyzed nucleophilic addition reaction. An enantioselective transformation of allylic alcohols into β-chiral saturated alcohols has been developed by combining two distinct metal- and organocatalyzed catalytic cycles. This waste-free triple cascade process merges an iron-catalyzed borrowing-hydrogen step with an aminocatalyzed nucleophilic addition Three is a lucky number: An enantioselective transformation of allylic alcohols into β-chiral saturated alcohols has been developed by combining two distinct metal- and organocatalyzed catalytic cycles. This waste-free triple cascade process merges an iron-catalyzed borrowing-hydrogen step with an aminocatalyzed nucleophilic addition reaction. Three is a lucky number: An enantioselective transformation of allylic alcohols into [beta]-chiral saturated alcohols has been developed by combining two distinct metal- and organocatalyzed catalytic cycles. This waste-free triple cascade process merges an iron-catalyzed borrowing-hydrogen step with an aminocatalyzed nucleophilic addition reaction. |
Author | Quintard, Adrien Rodriguez, Jean Constantieux, Thierry |
Author_xml | – sequence: 1 givenname: Adrien surname: Quintard fullname: Quintard, Adrien email: adrien.quintard-inv@univ-amu.fr organization: Aix-Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313, 13397, Marseille (France) http://ism2.univ-amu.fr/pages-bleues/index2.htm – sequence: 2 givenname: Thierry surname: Constantieux fullname: Constantieux, Thierry organization: Aix-Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313, 13397, Marseille (France) http://ism2.univ-amu.fr/pages-bleues/index2.htm – sequence: 3 givenname: Jean surname: Rodriguez fullname: Rodriguez, Jean email: jean.rodriguez@univ-amu.fr organization: Aix-Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313, 13397, Marseille (France) http://ism2.univ-amu.fr/pages-bleues/index2.htm |
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Copyright | Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Distributed under a Creative Commons Attribution 4.0 International License |
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Keywords | ORGANIC-SYNTHESIS C BOND FORMATION BORROWING HYDROGEN METAL-DIENE COMPLEXES ALPHA,BETA-UNSATURATED ALDEHYDES asymmetric catalysis dual catalysis hydrogen transfer MEDIATED 2+2+1 CYCLOADDITIONS OPPENAUER-TYPE OXIDATION IRON-CATALYST organocatalysis CARBON-MONOXIDE TRANSITION-METAL iron |
Language | English |
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Notes | ArticleID:ANIE201307295 Financial support from the Centre National de la Recherche Scientifique (CNRS) and Aix-Marseille Université is gratefully acknowledged. The authors gratefully thank Marion Jean and Nicolas Vanthuyne (Aix-Marseille Université) for chiral-phase HPLC analysis of all compounds. ark:/67375/WNG-7JQQDS5K-S Aix-Marseille Université Centre National de la Recherche Scientifique (CNRS) istex:D01222CFC128AC105801B1264083AC76D119DFA2 Financial support from the Centre National de la Recherche Scientifique (CNRS) and Aix‐Marseille Université is gratefully acknowledged. The authors gratefully thank Marion Jean and Nicolas Vanthuyne (Aix‐Marseille Université) for chiral‐phase HPLC analysis of all compounds. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
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Snippet | Three is a lucky number: An enantioselective transformation of allylic alcohols into β‐chiral saturated alcohols has been developed by combining two distinct... Three is a lucky number: An enantioselective transformation of allylic alcohols into β-chiral saturated alcohols has been developed by combining two distinct... Three is a lucky number: An enantioselective transformation of allylic alcohols into [beta]-chiral saturated alcohols has been developed by combining two... An enantioselective transformation of allylic alcohols into β-chiral saturated alcohols has been developed by combining two distinct metal- and organocatalyzed... |
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SubjectTerms | asymmetric catalysis Chemical Sciences Chemistry Chemistry, Multidisciplinary dual catalysis hydrogen transfer iron Organic chemistry organocatalysis Physical Sciences Science & Technology |
Title | An Iron/Amine-Catalyzed Cascade Process for the Enantioselective Functionalization of Allylic Alcohols |
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