Synthesis 2018; 50(04): 785-792
DOI: 10.1055/s-0036-1588547
paper
© Georg Thieme Verlag Stuttgart · New York

Multicatalytic Enantioselective Borrowing Hydrogen δ-Lactonization Strategy from β-Keto Esters and Allylic Alcohols

Adrien Quintard*
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille 13013, France   eMail: adrien.quintard@univ-amu.fr
,
Mylène Roudier
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille 13013, France   eMail: adrien.quintard@univ-amu.fr
,
Jean Rodriguez
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille 13013, France   eMail: adrien.quintard@univ-amu.fr
› Institutsangaben
The Centre National de la Recherche Scientifique (CNRS) and the Aix-Marseille Université (AMU), The Agence Nationale pour la Recherche (ANR-13-PDOC-0007-01) are gratefully acknowledged for financial support.
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Publikationsverlauf

Received: 15. Juni 2017

Accepted after revision: 19. Juli 2017

Publikationsdatum:
07. September 2017 (online)


Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry

Abstract

By combining an iron-catalyzed borrowing hydrogen of allylic alcohols with an enantioselective organocatalyzed Michael addition of β-keto esters followed by a subsequent DBU-promoted lactonization different enantioenriched δ-lactones have been synthesized with good enantioselectivities. The valuable building blocks, featuring in some cases challenging quaternary stereocenters, have been obtained with >90% ee.

Supporting Information

 
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