Towards Functionalized Silicon‐Containing  α‐ Amino Acids: Asymmetric Syntheses of Sila Analogs of Homoserine and Homomethionine | Zendy

Smith Richard J. | Zendy; Bienz Stefan | Zendy

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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.

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