Rondot Christophe, Retailleau Pascal, Zhu Jieping
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Org Lett. 2007 Jan 18;9(2):247-50. doi: 10.1021/ol0627202.
An efficient synthesis of chiral dihydrooxazines (2) from 1-aryl-2-amino-propane-1,3-diols (1) via the corresponding bistrichloroacetimidate intermediates has been developed. In this transformation, one trichloroacetimidate acts as a leaving group and the other acts as a nucleophile. The cyclization proceeds through an SN1 mechanism to provide trans-dihydrooxazines with complete diastereoselectivity irrespective of the absolute configuration of the benzylic alcohol. The transformation of 2 into other selectively protected aminodiols is also documented. [reaction: see text].
已开发出一种通过相应的双三氯乙酰亚胺酯中间体，由1-芳基-2-氨基丙烷-1,3-二醇（1）高效合成手性二氢恶嗪（2）的方法。在该转化过程中，一个三氯乙酰亚胺酯作为离去基团，另一个作为亲核试剂。环化反应通过SN1机制进行，无论苄醇的绝对构型如何，均可提供具有完全非对映选择性的反式二氢恶嗪。还记录了将2转化为其他选择性保护的氨基二醇的过程。[反应：见正文]
