Improved Synthesis of 5,5-Diamino BINAP and Application to Asymmetric Hydrogenation

• 作 者: 黄毅勇 邓国军 王霞瑜 何艳梅 范青华
• 机 构: College of Chemistry,Xiangtan University, Xiangtan, Hunan 411105, China,Center for Molecular Science
• 出 处: Chinese Journal of Chemistry
• 发表日期: 2004年09期
• 关键词: hydrogenation methoxyl chiral asymmetric naphthyl acrylic isopropyl anhydride ca

5,5-Diamino BINAP has been synthesized via three steps using BINAPO as starting material with high reaction yield. Present method needed only a stoichiometric quantity of nitric acid in the step of nitration of BINAPO, giving almost quantitative reaction yield. Based on 5,5-diamino BINAP, other three new BINAP derivatives have been synthesized. These modified BINAP ligands showed better catalytic properties as compared to BINAP itself in the asymmetric hydrogenation of 2-(6’-methoxyl-2’-naphthyl)acrylic acid.

5,5-Diamino BINAP has been synthesized via three steps using BINAPO as starting material with high reaction yield. Present method needed only a stoichiometric quantity of nitric acid in the step of nitration of BINAPO, giving almost quantitative reaction yield. Based on 5, These modified BINAP ligands showed better catalytic properties as BINAP itself in the asymmetric hydrogenation of 2- (6’-methoxyl-2’-naphthyl) acrylic acid.