(Wiley, 2018) Olaizola, Iurre; Campano, Teresa E.; Iriarte, Igor; Vera, Silvia; Mielgo, Antonia; García Castillo, Jesús María; Odriozola Ibarguren, José Manuel; Oiarbide, Mikel; Palomo, Claudio; Institute for Advanced Materials and Mathematics - INAMAT2; Química Aplicada; Kimika Aplikatua
The catalyst-controlled enantioselective direct addition reaction of enolizable esters and related carboxylic
acid derivatives to p electrophiles remains a difficult synthetic transformation. In this study, the suitability of a-hydroxy
ketones as ester equivalents capable of being activated by
bifunctional Brønsted base catalysts in the context of conjugate addition reactions to nitroolefins is demonstrated. The
scope of the reaction, which affords the corresponding Michael adducts with very high stereoselectivity (diastereomeric ratio (d.r.) +95:5, up to 99% enantiomeric excess (ee)),
and its limitations are explored, as is the aftermath elaboration of adducts into densely functionalized enantioenriched
products.