Wang Wei, Yang Jianqing, Ying Jinfa, Xiong Chiyi, Zhang Junyi, Cai Chaozhong, Hruby Victor J
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
J Org Chem. 2002 Sep 6;67(18):6353-60. doi: 10.1021/jo0203591.
A stereoselective method has been developed for the synthesis of 7- and 8-substituted dipeptide beta-turn mimetic azabicyclo[4.3.0]nonane amino acid esters. The allyl groups were introduced in high diastereoselectivity, controlled by 3-phenyl or 4-benzyl groups in pyroglutamic acid derivatives 3 or 9, respectively. The precursors, dehydroamino acids 7 and 13 derived from 5 or 11, underwent asymmetric hydrogenations with Burk's DuPHOS Rh(I)-based catalysts to furnish alpha-amino acid derivatives in high stereoselectivity. The resulting amino acids 8 and 14 were converted to the beta-turn mimetics 6,5-bicyclic lactams 1a-d in high yields.
已开发出一种立体选择性方法用于合成7-和8-取代的二肽β-转角模拟氮杂双环[4.3.0]壬烷氨基酸酯。通过焦谷氨酸衍生物3或9中的3-苯基或4-苄基分别控制，以高非对映选择性引入烯丙基。由5或11衍生的前体脱氢氨基酸7和13，用基于Burk的DuPHOS Rh(I)催化剂进行不对称氢化反应，以高立体选择性提供α-氨基酸衍生物。所得氨基酸8和14以高收率转化为β-转角模拟物6,5-双环内酰胺1a-d。
