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

Tetsuhiro Nemoto, Hiroyuki Kakei, Vijay Gnanadesikan, Shin Ya Tosaki, Takashi Ohshima, Masakatsu Shibasaki

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Abstract

The catalytic asymmetric epoxidation of α,β-unsaturated amides using Sm-BINOL-Ph3As=O 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.

Original languageEnglish
Pages (from-to)14544-14545
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number49
DOIs
Publication statusPublished - Dec 11 2002
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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