College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Org Lett. 2011 Nov 4;13(21):5920-3. doi: 10.1021/ol202573s. Epub 2011 Oct 13.
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 β-amino acid has been achieved by applying this method.
开发了一种高对映选择性和高效的合成光学活性同型烯丙胺的方法。该方法的关键特点包括：(1) 利用萘乙胺作为优秀的手性助剂和胺源；(2) 通过 N-酰亚胺离子的 1,3-手性诱导，具有高立体选择性和高产率；(3) 在温和条件下易于辅助去除，释放 N-Cbz 保护的同型烯丙胺。此外，通过应用该方法实现了所提出的新型含β-氨基酸的三肽的全合成。
