Amino-Zinc-Ene-Enolate Cyclization: A Short Access to cis-3-Substituted Prolino-homotryptophane Derivatives
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- 作者：Cé ; line Mothes ; Solange Lavielle ; Philippe Karoyan
- 刊名：Journal of Organic Chemistry
- 出版年：2008
- 出版时间：September 5, 2008
- 年：2008
- 卷：73
- 期：17
- 页码：6706-6710
- 全文大小：195K
- 年卷期：v.73,no.17(September 5, 2008)
- ISSN：1520-6904
文摘
Proline chimeras are useful tools for medicinal chemistry and/or biological applications. The asymmetric synthesis of cis-3-substituted prolines can be easily achieved via amino-zinc-ene-enolate cyclization followed by transmetalation of the cyclic zinc intermediate for further functionalization. Syntheses of prolino-homotryptophane derivatives were achieved through Negishi cross-coupling of the zinc intermediate with indole rings. The use of Pd catalyst derived from Fu’s [(t-Bu3)PH]-BF4 was required to avoid the undesired β-hydride elimination. Optically pure and orthogonally protected compounds were obtained readily usable for peptide synthesis.