33558-80-4Relevant academic research and scientific papers
Towards functionalized silicon-containing α-amino acids: Asymmetric syntheses of sila analogs of homoserine and homomethionine
Smith, Richard J.,Bienz, Stefan
, p. 1681 - 1696 (2007/10/03)
The homoserine and homomethionine sila analogs, (R)-HOSi(Me 2)CH2CH(NH2)CO2H ((R)-21) and (R)-MeSCH2Si(Me2)CH2CH(NH2)CO 2H ((R)-24), respectively, were each synthesized in nine steps and in 30 and 23% overall yield, respectively, from commercially available ClSiMe 2CH2Cl. The key step of both syntheses was the asymmetric α-bromination of an Evans amide to introduce the stereogenic center of the amino acids with defined absolute configuration. While the preparation of the homomethionine analog (R)-24 followed the expected pathway, the sila analog of homoserine, (R)-21, was unexpectedly formed during the catalytic hydrogenation of an N3CH2-substituted silane derivative.
