New chiral imino- and amino-sulfoxides as activators of allyl trichlorosilane in the asymmetric allylation of aldehydes

Chiral 2-methylsulfinyl benzaldehyde proved to be a valuable starting material for a convenient approach towards a variety of imino- and amino-sulfoxides. The catalytic properties of these new ligands, as potential activators of allyl trichlorosilane, have been exploited in new catalytic procedures for the synthesis of enantioenriched homoallylic alcohols.

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(R,R)-(+)-N1,N2-Bis-(2-(methylsulfinyl)-benzyl)-ethane-1,2-diamineC18H24N2O2S2Ee 99%[α]D = +69.0 (c 0.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(R)-(+)-N-(2-(Methylsulfinyl)benzylidene)(phenyl)methanamineC15H15NOSEe 99%[α]D = +190.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R,R)-(+)-N1,N2-Bis-(2-(methylsulfinyl)-benzyl)-ethane-1,2-dimethandiamine.C18H24N2O2S2Ee 99%[α]D = +103.0 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)

(R)-(+)-N-(2-(Methylsulfinyl)benzyl)(phenyl)methanamineC15H17NOSEe 99%[α]D = +29.6 (c 0.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-(+)-N-(2-(Methylsulfinyl)benzyl)-N-methyl(phenyl)methanamineC16H19NOSEe 99%[α]D = +55.5 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)