Stereocontrolled synthesis of quaternary β,γ-unsaturated amino acids:: chain extension of D- and L-α-(2-tributylstannyl)vinyl amino acids

被引：38

作者：

Berkowitz, DB ^{[1
]}

Chisowa, E ^{[1
]}

McFadden, JM ^{[1
]}

机构：

[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 30期

关键词：

self regeneration of stereocenters; beta; gamma-unsaturated amino acids; vinyl selenides; vinyl stannanes; chain extension;

D O I：

10.1016/S0040-4020(01)00499-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6329 / 6343

页数：15