Expedient Synthesis of Chiral Homoallylamines via N,O-Acetal TMS Ethers and Its Application

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• 作者：Young-Ger Suh ; Jaebong Jang ; Hwayoung Yun ; Sae Mi Han ; Dongyun Shin ; Jae-Kyung Jung ; Jong-Wha Jung
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：November 4, 2011
• 年：2011
• 卷：13
• 期：21
• 页码：5920-5923
• 全文大小：744K
• 年卷期：v.13,no.21(November 4, 2011)
• ISSN：1523-7052

文摘

A highly stereoselective and efficient method for the synthesis of optically active homoallylamines was developed. Key features of the method include (1) the utilization of naphthylethylamine as both an excellent chiral auxiliary and the amine source, (2) the 1,3-chiral induction of the N-acyliminium ion with high stereoselectivity and high yield, and (3) facile auxiliary removal under mild conditions to liberate N-Cbz-protected homoallylamines. In addition, the total synthesis of the proposed novel tripeptide containing a 尾-amino acid has been achieved by applying this method.