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Towards Functionalized Silicon‐Containing α‐ Amino Acids: Asymmetric Syntheses of Sila Analogs of Homoserine and Homomethionine
Author(s) -
Smith Richard J.,
Bienz Stefan
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490152
Subject(s) - chemistry , stereocenter , stereochemistry , yield (engineering) , homoserine , silane , amide , halogenation , derivative (finance) , amino acid , absolute configuration , catalysis , enantioselective synthesis , medicinal chemistry , organic chemistry , biochemistry , materials science , quorum sensing , virulence , economics , financial economics , metallurgy , gene
The homoserine and homomethionine sila analogs, ( R )‐HOSi(Me 2 )CH 2 CH(NH 2 )CO 2 H (( R )‐ 21 ) and ( R )‐MeSCH 2 Si(Me 2 )CH 2 CH(NH 2 )CO 2 H (( R )‐ 24 ), respectively, were each synthesized in nine steps and in 30 and 23% overall yield, respectively, from commercially available ClSiMe 2 CH 2 Cl. 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 N 3 CH 2 ‐substituted silane derivative.