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Synlett 2016; 27(11): 1699-1702
DOI: 10.1055/s-0035-1561956
DOI: 10.1055/s-0035-1561956
letter
A Formal Enantioselective Synthesis of (–)-Epiquinamide by Proline-Catalyzed One-Pot Sequential α-Amination/Propargylation of Aldehyde and Asymmetric Dihydroxylation of Olefin
Authors
Further Information
Publication History
Received: 09 November 2015
Accepted after revision: 04 March 2016
Publication Date:
07 April 2016 (online)
Abstract
Two independent routes to the formal synthesis of (–)-epiquinamide, have been described: the first route utilizes an l -proline-catalyzed one-pot sequential α-amination/propargylation of aldehyde, while the second one employs asymmetric dihydroxylation as the key reaction to install the stereochemistry. While the first synthesis was accomplished in nine steps with 24.4% overall yield and dr 9:1, the second strategy resulted in the synthesis in eight steps with 36.4% overall yield and with perfect enantiocontrol.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561956.
- Supporting Information (PDF)
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