Diastereoselective Michael Addition of Nitromethane to Enoates Derived From (R)-Glyceraldehyde Acetonide

Vera L. Patrocinio; Paulo R. R. Costa; Carlos R. D. Correia

doi:10.1055/s-1994-25504

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Synthesis 1994; 1994(5): 474-476
DOI: 10.1055/s-1994-25504

short paper

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Diastereoselective Michael Addition of Nitromethane to Enoates Derived From (R)-Glyceraldehyde Acetonide

Vera L. Patrocinio^* , Paulo R. R. Costa, Carlos R. D. Correia

^*Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brasil

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Publikationsdatum:
17. September 2002 (online)

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The Michael addition of nitromethane to enoates derived from glyceraldehyde acetonide leads to syn-adducts 3 with high diastereoselectivity (de 76-90 %). The stereochemistry of the new stereogenic center was determined by transforming the Michael adduct 3b into lactone 6a.