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Synthesis 2018; 50(04): 785-792
DOI: 10.1055/s-0036-1588547
DOI: 10.1055/s-0036-1588547
paper
Multicatalytic Enantioselective Borrowing Hydrogen δ-Lactonization Strategy from β-Keto Esters and Allylic Alcohols
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.Weitere Informationen
Publikationsverlauf
Received: 15. Juni 2017
Accepted after revision: 19. Juli 2017
Publikationsdatum:
07. September 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201804/lookinside/thumbnails/ss-2017-z0399-op_10-1055_s-0036-1588547-1.jpg)
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.
Key words
organocatalysis - iron catalysis - lactone synthesis - borrowing hydrogen - multi-catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588547.
- Supporting Information
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- 11 We are not aware of such challenging lactonization on non-substituted keto esters.
For pioneering work on borrowing hydrogen, see:
For reviews on the topic, see:
For a highlight and review on this challenging topic, see:
For examples of enantioselective borrowing hydrogen transformations, see:
For other type of enantioselective hydrogen transfer initiated reactions, see:
For examples of spirolactones, see:
For a review on the iron complex used herein, see:
For selected examples, see:
For examples of spirolactonization, see:
For other examples of copper co-catalyzed activation, see: