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Allylation of sulfonimines

Allylation of aldimines and sulfonimines with indium powder in poly(propylene) glycol (MW 1000), a benign and recyclable reaction medium, results in the formation of the corresponding homoallylic amines and sulfonamides in high yields (Equation (62)).265... [Pg.690]

Examples of imine allylation in aqueous media are rather limited compared with the carbonyl version. This is ascribed to the lower electrophilicity of the C=N function of imines and its ease of hydrolysis to carbonyl compounds. In order to overcome the undesired side-reactions, sulfonimines in place of simple imines are success-fully used for the allylation under aqueous conditions (Equation (61)). Grotylation of cr-sulfonimino esters gives... [Pg.690]

Sulfonimines (24) with a pendant ort/io-Michael acceptor (Z = COR, CHO, NO2, SO2R) undergo nucleophilic addition (Nu = Ar, heteroAr, CN, allyl, propargyl, enolate adduct = 25) subsequent intramolecular aza-Michael reaction (IMAMR) yields 1,3-disubstituted isoindolines (26) in good yield and de. Cis- and trans-products can be 0 selected kinetically or thermodynamically, sometimes by choice of base. The products can be readily desulfonated. [Pg.12]

See other pages where Allylation of sulfonimines is mentioned: [Pg.351]    [Pg.332]    [Pg.103]    [Pg.443]    [Pg.114]    [Pg.351]    [Pg.332]    [Pg.103]    [Pg.443]    [Pg.114]    [Pg.180]    [Pg.196]    [Pg.103]   
See also in sourсe #XX -- [ Pg.332 ]

See also in sourсe #XX -- [ Pg.332 ]



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Sulfonimines

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