Synthesis of (-)-(4R,5R)-4,5-bis[di-3′-(2′,6′-dimethoxypyridyl)phosphinomethyl]-2,2-dimethyl-1,3-dioxolane and its application in the Rh-catalyzed asymmetric hydrogenation reactions

被引：30
作者：
Hu, WH
Chen, CC
Xue, GP
Chan, ASC [1 ]
机构：
[1] Hong Kong Polytech Univ, Union Lab Asymmetr Synth, Hong Kong, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 23期
关键词：
D O I：
10.1016/S0957-4166(98)00457-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The chiral ligand (-)-(4R,5R)-4,5-bis[di-3'-(2',6'-dimethoxypyridyl)phosphinomethyl]-2, 2-dimethyl-1,3-dioxolane 3 [(R,R)-Py*-DIOP] was synthesized via a key intermediate bis[3-(2,6-dimethoxypyridyl)]phosphine-borane 9. The asymmetric hydrogenation of prochiral olefins was investigated using a rhodium catalyst containing 3. For the hydrogenation of amidoacrylic acids, enols and itaconic acid, while the enantioselectivity of [Rh-(R,R)-Py*-DIOP] was similar to that of [Rh-(R,R)-DIOP] the absolute configurations of the products from the two catalyst systems were found to be opposite. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4183 / 4192
页数：10
相关论文
共 50 条
[41]   (-)-(4S,5R)-4-(2-PYRIDYL+-5-(DIPHENYLPHOSPHINO)METHYL-2,2-DIMETHYL-1,3-DIOXOLANE A NEW CHIRAL LIGAND FOR ENANTIOSELECTIVE CATALYSIS [J].
CHELUCCI, G ;
CABRAS, MA ;
BOTTEGHI, C ;
MARCHETTI, M .
TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :299-302
[42]   X-RAY STRUCTURAL CHARACTERIZATION AND CATALYTIC PROPERTIES OF HYDRIDOBIS[4,5-BIS((DIPHENYLPHOSPHINO)METHYL)-2,2-DIMETHYL-1,3-DIOXOLANE]RHODIUM(I) [J].
BALL, RG ;
JAMES, BR ;
MAHAJAN, D ;
TROTTER, J .
INORGANIC CHEMISTRY, 1981, 20 (01) :254-261
[43]   Asymmetric hydrogen-transfer hydrogenation on rhodium(I) complexes with new optically active salen ligands derived from (4S,5S)-4,5-bis(aminomethyl)-2,2-dimethyl-1,3-dioxolane [J].
L. O. Nindakova ;
B. A. Shainyan ;
N. M. Badyrova ;
F. M. Lebed’ .
Russian Journal of Organic Chemistry, 2012, 48 :59-63
[44]   Asymmetric Hydrogen-Transfer Hydrogenation on Rhodium(I) Complexes with New Optically Active Salen Ligands Derived from (4S,5S)-4,5-Bis(aminomethyl)-2,2-dimethyl-1,3-dioxolane [J].
Nindakova, L. O. ;
Shainyan, B. A. ;
Badyrova, N. M. ;
Lebed, F. M. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (01) :59-63
[45]   (S)-3-Dimethylamino-2-{(4S, 5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxypropanoic acid [J].
Jenkinson, Sarah F. ;
Hotchkiss, David J. ;
Cowley, Andrew R. ;
Fleet, George W. J. ;
Watkin, David J. .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 :O294-U5289
[46]   (4R,5R)-2,2-dimethyl-α,α,α′,α′-tetra(naphth-2-yl)-1,3-dioxolane-4,5-dimethanol from dimethyl tartrate and 2-naphthylmagnesium bromide [J].
Beck, AK ;
Gysi, P ;
La Vecchia, L ;
Seebach, D .
ORGANIC SYNTHESES, VOL 76 - 1999, 1999, 76 :12-22
[47]   Syntheses, crystal structures and fluorescent properties of R,R-DIOP based copper (I) and cadmium (II) complexes [R,R-DIOP = (4R,5R)-trans-4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxalane} [J].
Li, Jun-Xia ;
Du, Zhong-Xiang ;
An, Hui-Qin ;
Zhou, Jian ;
Dong, Jian-Xun ;
Wang, Shu-Rong ;
Zhu, Bao-Lin ;
Zhang, Shou-Min ;
Wu, Shi-Hua ;
Huang, Wei-Ping .
JOURNAL OF MOLECULAR STRUCTURE, 2009, 935 (1-3) :161-166
[48]   CRYSTAL AND MOLECULAR-STRUCTURE OF TRANS-CHLOROHYDRIDOBIS[(+)-4,5-BIS((DIPHENYLPHOSPHINO)METHYL)-2,2-DIMETHYL-1,3-DIOXOLANE]RUTHENIUM(II) TOLUENE SOLVATE [J].
BALL, RG ;
TROTTER, J .
INORGANIC CHEMISTRY, 1981, 20 (01) :261-265
[49]   (E)-2-((4R, 5R)-5-((Benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-ene-1,4-diol [J].
Carreras, Carlos R. ;
Garcia, Celina E. ;
Martin, Victor S. ;
Tonn, Carlos E. ;
Diaz Diaz, David ;
Pedro Cenal, Juan .
MOLBANK, 2010, (02)
[50]   Host-guest chemistry. The structure and proton disorder of the three-component crystal formed by 3(5)-methyl-4-nitropyrazole, (R,R)-(-)-trans-4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane and toluene [J].
Toda, F ;
Tanaka, K ;
FocesFoces, C ;
Infantes, L ;
Claramunt, RM ;
Lopez, C ;
Elguero, J .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1996, 9 (09) :611-618
12345