Catalytic Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides with Vinyl Sulfones
2006; American Chemical Society; Volume: 8; Issue: 9 Linguagem: Inglês
10.1021/ol060314c
ISSN1523-7060
AutoresTomás Llamas, Ramón Goméz Arrayás, Juan C. Carretero,
Tópico(s)Asymmetric Synthesis and Catalysis
Resumo[reaction: see text] A general protocol for the enantioselective catalytic 1,3-dipolar cycloaddition of azomethine ylides with aryl vinyl sulfones is described. Nearly complete exo selectivity and enantioselectivities up to 85% ee are attained with Cu(CH(3)CN)(4)ClO(4)/Taniaphos as the catalyst system. The resulting enantioenriched 3-sulfonyl cycloadducts are versatile intermediates in the synthesis of 2,5-disubstituted pyrrolidines.
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