Catalytic Asymmetric Epoxidation of α,β-Unsaturated Amides: Efficient Synthesis of β-Aryl α-Hydroxy Amides Using a One-Pot Tandem Catalytic Asymmetric Epoxidation−Pd-Catalyzed Epoxide Opening Process
- 13 November 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (49) , 14544-14545
- https://doi.org/10.1021/ja028454e
Abstract
The catalytic asymmetric epoxidation of α,β-unsaturated amides using Sm−BINOL−Ph3AsO complex was succeeded. Using 5−10 mol % of the asymmetric catalyst, a variety of amides were epoxidized efficiently, yielding the corresponding α,β-epoxy amides in up to 99% yield and in more than 99% ee. Moreover, the novel one-pot tandem process, one-pot tandem catalytic asymmetric epoxidation−Pd-catalyzed epoxide opening process, was developed. This method was successfully utilized for the efficient synthesis of β-aryl α-hydroxy amides, including β-aryllactyl-leucine methyl esters. Interestingly, it was found that beneficial modifications on the Pd catalyst were achieved by the constituents of the first epoxidation, producing a more suitable catalyst for the Pd-catalyzed epoxide opening reaction in terms of chemoselectivity.Keywords
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