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Stereocontrolled Synthesis of Quaternary β,γ-Unsaturated Amino Acids: Chain Extension of D- & L- α-(2-Tributylstannyl)Vinyl Amino Acids.
- Source :
-
Tetrahedron [Tetrahedron] 2001 Jul 23; Vol. 57 (30), pp. 6329-6343. - Publication Year :
- 2001
-
Abstract
- A pair of diastereomeric (4S,5S)- and (4S,5R)-4-methoxycarbonyl-5-phenylselenomethyl-2-phenyl oxazolines, derived from L-vinylglycine, serve as precursors to protected, quaternary, L- and D-α-(2-tributylstannyl)vinyl amino acids, respectively, in three steps {(i) alkylative side chain installation, (ii) eliminative ring-opening and (iii) vinyl selenide to vinyl stannane interconversion}. The title compounds may be protodestannylated to the corresponding free, quaternary L- and D-vinyl amino acids. Alternatively, the 2-stannylvinyl α-branch (or the derivative 2-iodovinyl branch) may be exploited to access novel quaternary, L- and D-β,γ-unsaturated amino acids via a range of transition metal-mediated cross coupling reactions.
Details
- Language :
- English
- ISSN :
- 0040-4020
- Volume :
- 57
- Issue :
- 30
- Database :
- MEDLINE
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 29973743
- Full Text :
- https://doi.org/10.1016/S0040-4020(01)00499-9