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Synlett 2020; 31(01): 60-64
DOI: 10.1055/s-0039-1690264
DOI: 10.1055/s-0039-1690264
letter
Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst
We are grateful to the National Key Technology Research and Development Program of China for financial support (No. 2017YFD0201404).Weitere Informationen
Publikationsverlauf
Received: 28. August 2019
Accepted after revision: 22. Oktober 2019
Publikationsdatum:
03. Dezember 2019 (online)
![](https://www.thieme-connect.de/media/synlett/202001/lookinside/thumbnails/st-2019-r0453-l_10-1055_s-0039-1690264-1.jpg)
Abstract
A novel and highly enantioselective synthesis of hydroxyalkynyl esters and ethers through the asymmetric addition of alkynyl esters or ethers to aldehydes promoted by a cyclopropyl amino alcohol based zinc catalyst has been developed. The method afforded a library of new enantioenriched hydroxyalkynol esters and ethers (up to 93% yield; 95% ee), and it was compatible with a broad range of functional groups. Moreover, it could be used in the synthesis of carbon-chain-elongated enantioenriched hydroxyalkynol esters and (2R,5R)-musclide-A1, a cardiotonic potentiating principle from musk.
Key words
zinc catalysis - hydroxyalkynyl esters - hydroxyalkynyl ethers - alkynylation - musclide-A1 - asymmetric catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690264.
- Supporting Information
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References and Notes
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