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  • Title: Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters.
    Author: Davis FA, Qiu H, Song M, Gaddiraju NV.
    Journal: J Org Chem; 2009 Apr 03; 74(7):2798-803. PubMed ID: 19271739.
    Abstract:
    Addition of vinylaluminum NMO reagents to N-(p-toluenesufinyl)- and N-(2-methypropanesulfinyl)-derived sulfinimines gives N-sulfinyl aza-Morita-Baylis-Hillman products (dr = 7:1 to 12:1) that result from addition of the reagent from the least hindered direction. Hydrogenation of the aza-MBH adducts with a Rh(I) catalyst affords anti-alpha-substituted N-sulfinyl-beta-amino esters in good yield and high dr (10:1 to 21:1).
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