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- W2031972008 abstract "The diastereo- and enantioselective addition of N-heterocyclic carbene-generated homoenolates to nitrones is reported. This formal [3 + 3] addition of α,β-unsaturated aldehydes and nitrones generates unusual morpholinone heterocycles which are converted into γ-hydroxy amino esters by addition of methanol to the reaction. The use of a chiral N-heterocyclic carbene (NHC) as the catalyst provides the amino esters in high diastereoselectivity (up to 20:1 dr) and enantioselectivity (up to 94%). The process accommodates α,β-unsaturated aldehydes with β-alkyl and β-aryl substituents. The γ-hydroxy amino esters can be converted to optically enriched γ-lactams by a two-step procedure involving mild reduction of the N−O bond and acid-catalyzed amide formation." @default.
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- W2031972008 date "2008-01-31" @default.
- W2031972008 modified "2023-10-03" @default.
- W2031972008 title "Highly Diastereo- and Enantioselective Additions of Homoenolates to Nitrones Catalyzed by <i>N</i>-Heterocyclic Carbenes" @default.
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- W2031972008 doi "https://doi.org/10.1021/ja710521m" @default.
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