Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of N-Acylthiazolidinethiones

David A Evans, Reagan J Thomson

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60 Scopus citations

Abstract

The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51−92% yield, 90−99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.
Original languageEnglish
Pages (from-to)10506-7
JournalJournal of the American Chemical Society
Volume127
StatePublished - Jul 8 2005

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