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Synthesis 2016; 48(19): 3207-3216
DOI: 10.1055/s-0035-1561468
DOI: 10.1055/s-0035-1561468
paper
Asymmetric Synthesis of Tetrahydrobenzofurans and Annulated Dihydropyrans via Cooperative One-Pot Organo- and Silver-Catalysis
Further Information
Publication History
Received: 29 April 2016
Accepted: 02 May 2016
Publication Date:
23 June 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201619/lookinside/thumbnails/ss-2016-z0305-op_10-1055_s-0035-1561468-1.jpg)
In memory of Professor Jean Normant
Abstract
A low catalyst loading of a squaramide (0.5 mol%) and a silver(I) salt (1 mol%) efficiently catalyzes a one-pot asymmetric Michael addition/hydroalkoxylation reaction between 1,3-diketones and alkyne-tethered nitroalkenes. Depending on the 1,3-dicarbonyl substrate this cooperative catalytic approach opens access to tetrahydrobenzofurans or annulated dihydropyrans in moderate to excellent yields and very good to excellent enantioselectivities.
Key words
asymmetric synthesis - organocatalysis - one-pot synthesis - silver catalysis - annulationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561468.
- Supporting Information
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For examples of merging organo- and transition metal-catalysis, see: