Diastereoselective Synthesis of δ-Aminoacids through Domino Ireland−Claisen Rearrangement and Michael Addition
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- 作者：Narciso M. Garrido ; Mercedes Garcí ; a ; David Dí ; ez ; M. Rosa Sá ; nchez ; F. Sanz ; Julio G. Urones
- 刊名：Organic Letters
- 出版年：2008
- 出版时间：May 1, 2008
- 年：2008
- 卷：10
- 期：9
- 页码：1687 - 1690
- 全文大小：135K
- 年卷期：v.10,no.9(May 1, 2008)
- ISSN：1523-7052
文摘
A novel domino reaction
stereoselective Ireland−Claisen rearrangement and asymmetric Michael additionis described. A protocol starting from Baylis−Hillman adducts 3a−f using chiral lithium amide affords optically active γ-substituted δ-aminoacids 4a−f with high diastereoselectivities and enantioselectivities. The acid can be isolated easily from large-scale reactions and transformed to 2,3-disubstituted piperidines 11 or 2-substituted nipecotic acid derivates 12.