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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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 52; no. 49; pp. 12883 - 12887
Main Authors Quintard, Adrien, Constantieux, Thierry, Rodriguez, Jean
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 02.12.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Wiley-VCH Verlag
EditionInternational ed. in English
Subjects
asymmetric catalysis
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
dual catalysis
hydrogen transfer
iron
Organic chemistry
organocatalysis
Physical Sciences
Science & Technology
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
Online AccessGet full text
ISSN1433-7851
1521-3773
1521-3773
DOI10.1002/anie.201307295

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Summary: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.
Bibliography: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.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201307295