Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe
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- 作者：Stephen G. Davies ; Ai M. Fletcher ; Gesine J. Hermann ; Giovanna Poce ; Paul M. Roberts ; Andrew D. Smith ; Miles J. Sweet ; James E. Thomson
- 刊名：Tetrahedron: Asymmetry
- 出版年：2010
- 出版时间：14 July 2010
- 年：2010
- 卷：21
- 期：13-14
- 页码：1635-1648
- 全文大小：2139 K
文摘
The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The β-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an α,β,α-pseudotripeptide.