Ir-Catalyzed Enantioselective Hydrogenation of 2H-1,4-Benzoxazines with a Chiral 1,2,3,4- Tetrahydro-l-naphthylamine Derived Phosphine-aminophosphine Ligand
Ir-Catalyzed Enantioselective Hydrogenation of 2H-1,4-Benzoxazines with a Chiral 1,2,3,4- Tetrahydro-l-naphthylamine Derived Phosphine-aminophosphine Ligand
摘要
Unsymmetrical hybrid chiral phosphine-aminophosphine ligand derived from 1,2,3,4-tetrahydro-l-naphthyl- amine has been found to be highly efficient in the Ir-catalyzed asymmetric hydrogenation of various 3-aryl-2H-1,4-benzoxazines, providing good enantioselectivities (up to 95% ee) and high catalytic activity (S/C up to 5000).
Unsymmetrical hybrid chiral phosphine-aminophosphine ligand derived from 1,2,3,4-tetrahydro-l-naphthyl- amine has been found to be highly efficient in the Ir-catalyzed asymmetric hydrogenation of various 3-aryl-2H-1,4-benzoxazines, providing good enantioselectivities (up to 95% ee) and high catalytic activity (S/C up to 5000).
参考文献37
-
1(a) Blaser, H.-U.; Spinder, F. In Handbook of Homogeneous Hydrogenation, Eds.: de Vries, J. G.; Elsevier, C. J., Wiley-VCH, Wein-heim, 2007.
-
2Fleury-Bregeot, N.; de la Fuente, V.; Castillon, S.; Claver, C. ChemCatChem 2010, 2, 1346.
-
3Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713.
-
4Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron'. Asymmetry 1998, 9, 2657.
-
5Gao, K.; Yu, C.-B.; Wang, D.-S.; Zhou, Y.-G. Adv. Synth. Catal.2012,354,483.
-
6(a) Brown, K. S.; Djerassi, C. J. Am. Chem. Soc. 1964, 86, 2451.
-
7Belattar, A.; Saxton, J. E. J. Chem. Soc., Perkin Trans. 1 1992, 679.
-
8Daiichi, S. Drugs Future 1992, 17, 559.
-
9Shim, J. Y.; Collantes, E. R.; Welsh, W. J. J. Med. Chem. 1998, 41, 4521.
-
10Charushin, V. N.; Krasnov, V. P.; Levit, G. L.; Korolyova, M. A.; Kodess, M. I.; Chupakhin, O. N.; Kim, M. H.; Lee, H. S.; Park, Y. J.; Kim, K. C. Tetrahedron: Asymmetry 1999, 10, 2691.
-
1Jian Hong Liu,Dong Liang,Bin Bin Fan,Rui Feng Li,Hua Chen.Enantioselective hydrogenation of acetophenone by(1S,2S)-DPEN-Ru(Ⅱ)Cl_2(PPh_3)_2 encapsulated in Al-MCM-41[J].Chinese Chemical Letters,2010,21(7):802-806. 被引量:1
-
2蒋海珍,任仲皎,万文,石龙冈.An Improved Synthesis of Azines under Solvent-Free Conditions[J].Journal of Shanghai University(English Edition),2005,9(4):369-371.
-
3王琦玲,赵勃,李玲.苯并恶嗪的不同合成法及其表征[J].化工中间体,2011,7(8):35-37.
-
4Cherkupally Sanjeeva Reddy,Mekala Raghu.Synthesis of some new N,N'-diarylsubstituted methylene-bis-dihydro-2H-1,3-benzoxazines[J].Chinese Chemical Letters,2008,19(12):1407-1410.
-
5韩英锋,杨定乔,徐峰,董建霞.铑催化不对称氢化反应的研究进展[J].化工时刊,2004,18(11):1-7. 被引量:2
-
6Bao Han XIE,Shi Jie LU,Hong Xiang FU,Lan Yong GAO (State Key Laboratory for Oxo Srnthesis and Selective Oxidation Lanzhou Institute of Chemical Physics. Chinese Academy of Sciences, Lanzhou 730000).Enantioselective Hydrogenation of α,β-Unsaturated Cyclic Ketones by Double Asymmetric Induction Preparation of (R)-Muscone[J].Chinese Chemical Letters,1997,8(6):477-478. 被引量:1
-
7付慧英,宋群梁,孙晓宇,侯晓远,肖斐,邵丙铣.Photovoltaic Characteristics of a Naphthylamine Derivative[J].Chinese Journal of Chemistry,2007,25(9):1242-1245.
-
8N—乙基—α—萘胺合成工艺优化[J].精细化工经济与技术信息,1994(7):22-23.
-
9杨先金,刘金涛.Synthesis of Fluoroalkylated Heterocycles via the Reaction of 3-(1-Hydropolyfluoroalkenyl)-l-oxo-2,4,1-benzoxazines with Dinucleophilic Reagents[J].Chinese Journal of Chemistry,2006,24(10):1418-1420.
-
10粒状苯并恶嗪中间体[J].现代化工,2002,22(8):69-69.