1621104-67-3Relevant articles and documents
α-Hydroxy Ketones as Masked Ester Donors in Br?nsted Base Catalyzed Conjugate Additions to Nitroalkenes
Olaizola, Iurre,Campano, Teresa E.,Iriarte, Igor,Vera, Silvia,Mielgo, Antonia,García, Jesús M.,Odriozola, José M.,Oiarbide, Mikel,Palomo, Claudio
supporting information, p. 3893 - 3901 (2018/03/21)
The catalyst-controlled enantioselective direct addition reaction of enolizable esters and related carboxylic acid derivatives to π electrophiles remains a difficult synthetic transformation. In this study, the suitability of α-hydroxy ketones as ester equivalents capable of being activated by bifunctional Br?nsted 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.
