期刊
TETRAHEDRON
卷 57, 期 30, 页码 6329-6343出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00499-9
关键词
self regeneration of stereocenters; beta,gamma-unsaturated amino acids; vinyl selenides; vinyl stannanes; chain extension
资金
- NCI NIH HHS [R29 CA062034] Funding Source: Medline
A pair of diastereomeric (4S,5S)- and (4S,SR)-4-methoxycarbonyl-5-phenylselenomethyl-2-phenyl oxazolines, derived from L-vinylglycine, serve as precursors to protected, quaternary, L- and D-alpha-(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 alpha -branch (or the derivative 2-iodovinyl branch) may be exploited to access novel quaternary, L- and D-beta,gamma -unsaturated amino acids via a range of transition metal-mediated cross-coupling reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.
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