Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States.
Org Lett. 2015 Aug 7;17(15):3778-81. doi: 10.1021/acs.orglett.5b01755. Epub 2015 Jul 22.
The development and application of a new generation of non-C2-symmetric ProPhenol ligands is reported herein. Rational design of the ProPhenol ligand paved the way to the first catalytic and asymmetric vinylation of N-Boc imines via hydrozirconation giving rise to valuable allylic amines in excellent yields and enantioselectivities. The utility of this method was demonstrated by developing the shortest reported asymmetric synthesis of the selective serotonine reuptake inhibitor (SSRI) (-)-dapoxetine.
本文报道了新一代非 C2 对称 ProPhenol 配体的开发和应用。ProPhenol 配体的合理设计为通过氢化锆反应首次实现 N-Boc 亚胺的催化和不对称乙烯基化铺平了道路，以优异的收率和对映选择性得到了有价值的烯丙基胺。该方法的实用性通过开发选择性血清素再摄取抑制剂（SSRI）（-）-达泊西汀的最短报道不对称合成得到了证明。
