New unsaturated amino acids containing an allylsilane moiety on the lateral chain

New enantiomerically enriched polyfunctionalized allylsilanes have been obtained from the synthetic elaboration of naturally occurring serine. In particular, an oxazolidine bearing an allylsilane framework on the lateral chain proved to be a suitable precursor for the corresponding silylated vinyl glycine derivatives.

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(4R)-2,2-Dimethyl-4-(E-3-trimethylsilanyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl esterC16H31NO3Si[α]D26=-22.0 (c 1.31, CHCl3)Source of chirality: l-serineAbsolute configuration: (R)

(4R)-2,2-Dimethyl-4-(3-trimethylsilanyl-prop-1-ynyl)-oxazolidine-3-carboxylic acid tert-butyl esterC16H29NO3Si[α]D24=-108.5 (c 1.38, CHCl3)Source of chirality: l-serineAbsolute configuration: (R)

(4R)-2,2-Dimethyl-4-(Z-3-trimethylsilanyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl esterC16H31NO3Si[α]D25=-152.3 (c 0.7, CHCl3)Source of chirality: l-serineAbsolute configuration: (R)

(2R)-2-tert-Butoxycarbonylamino-5-trimethylsilanyl-E-pent-3-enoic acid methyl esterC13H27NO3Si[α]D24=-125.4 (c 0.69, CHCl3)Source of chirality: l-serineAbsolute configuration: (R)

(2R)-2-tert-Butoxycarbonylamino-5-trimethylsilanyl-Z-pent-3-enoic acid methyl esterC13H27NO3Si[α]D24=-81.2 (c 0.52, CHCl3)Source of chirality: l-serineAbsolute configuration: (R)

(2S,2′R)-2-(2′-tert-Butoxycarbonylamino-5-trimethylsilanyl-E-pent-3-enoylamino)-3-phenyl-propionic acid methyl esterC23H36N2O5Si[α]D25=-11.2 (c 0.69, CHCl3)Source of chirality: l-serine, l-phenylalanineAbsolute configuration: (2S,2′R)