Synthesis
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*, Mylène Roudier, Jean Rodriguez
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.
Further Information

Publication History

Received: 15 June 2017

Accepted after revision: 19 July 2017

Publication Date:
07 September 2017 (eFirst)

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