Novel 1,3,2-diazaphospholidines with pseudodipeptide substituents

被引:1
作者
Chuchelkin, I. V. [1 ]
Gavrilov, V. K. [1 ]
Firsin, I. D. [1 ]
Zimarev, V. S. [1 ]
Novikov, I. M. [1 ]
Maksimova, M. G. [1 ]
Shiryaev, A. A. [1 ]
Zheglov, S. V. [1 ]
Tafeenko, V. A. [2 ]
Chernyshev, V. V. [2 ]
Gavrilov, K. N. [1 ]
机构
[1] Ryazan State Univ, Chem Dept, 46 Svoboda St, Ryazan 390000, Russia
[2] Lomonosov Moscow State Univ, Dept Chem, GSP 1, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
Chiral; 1; 3; 2-diazaphospholidine; pseudodipeptide; Pd-catalyzed asymmetric allylation; Rh-catalyzed asymmetric hydrogenation; ENANTIOSELECTIVE ALLYLATION; CONTAINING LIGANDS; PALLADIUM; EFFICIENT; DERIVATIVES;
D O I
10.1080/10426507.2018.1540484
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral 1,3,2-diazaphospholidine with pseudodipeptide substituents was prepared. This asymmetric inducer provided up to 84% ee in the Pd-catalyzed asymmetric allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate, and up to 53% ee in the Rh-catalyzed asymmetric hydrogenation of (Z)-methyl 2-acetamido-3-phenylacrylate. [GRAPHICS] .
引用
收藏
页码:493 / 496
页数:4
相关论文
共 37 条
[1]  
[Anonymous], 2012, Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis
[2]   Modular Synthesis of Novel Chiral Phosphorous Triamides Based on (S)-N-(Pyrrolidin-2-ylmethyl)aniline and Their Application in Asymmetric Catalysis [J].
Barta, Katalin ;
Hoelscher, Markus ;
Francio, Giancarlo ;
Leitner, Walter .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (24) :4102-4116
[3]   Supramolecular Self-Assembled Ligands in Asymmetric Transition Metal Catalysis [J].
Bellini, Rosalba ;
van der Vlugt, Jarl Ivar ;
Reek, Joost N. H. .
ISRAEL JOURNAL OF CHEMISTRY, 2012, 52 (07) :613-629
[4]  
Borner A., 2008, Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications
[5]   Palladium allylic complexes with enantiopure bis(diamidophosphite) ligands bearing a cyclohexane-1,2-diamine skeleton as catalysts in the allylic substitution reaction [J].
Bravo, Maritza J. ;
Ceder, Rosa M. ;
Grabulosa, Arnald ;
Muller, Guillermo ;
Rocamora, Merce ;
Font-Bardia, Merce .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 830 :42-55
[6]   New Enantiopure P,P-Bidentate Bis(diamidophosphite) Ligands. Application in Asymmetric Rhodium-Catalyzed Hydrogenation [J].
Bravo, Maritza J. ;
Ceder, Rosa M. ;
Muller, Guillermo ;
Rocamora, Merce .
ORGANOMETALLICS, 2013, 32 (09) :2632-2642
[7]   Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to enones with new peptidyl phosphane ligands [J].
Breit, B ;
Laungani, AC .
TETRAHEDRON-ASYMMETRY, 2003, 14 (24) :3823-3826
[8]   A practical method for the large-scale synthesis of diastereomerically pure (2R,5S)-3-phenyl-2-(8-quinolinoxy)-1,3-diaza-2-phosphabicyclo-[3.3.0]-octane ligand (QUIPHOS).: Synthesis and X-ray structure of its corresponding chiral π-allyl palladium complex [J].
Brunel, JM ;
Constantieux, T ;
Buono, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8940-8942
[9]   Supramolecular ligand-ligand and ligand-substrate interactions for highly selective transition metal catalysis [J].
Carboni, Stefano ;
Gennari, Cesare ;
Pignataro, Luca ;
Piarulli, Umberto .
DALTON TRANSACTIONS, 2011, 40 (17) :4355-4373
[10]   Efficient and mild method for preparation of allylic amines from aziridine-2-alcohols using PPh3/I2/imidazole [J].
Chavan, Subhash P. ;
Khairnar, Lalit B. ;
Chavan, Prakash N. .
TETRAHEDRON LETTERS, 2014, 55 (43) :5905-5907