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
[31]   Synthesis and Characterization of (4R,5R)-1,3-dioxolance-4,5-bis(2-pyridineacrboxylic acid) [J].
Jiang Yan ;
Bu Yun-Fei ;
Zhang Zhi-Hui ;
Wang Le-Yong ;
Sun Xiao-Qiang .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2011, 30 (09) :1221-1224
[32]   Influence of exposure and infusion times on the cytotoxicity and pharmacokinetics of cis-malonato[(4R, 5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]platinum(II) [J].
Kim, HT ;
Kim, DK ;
Cho, YB ;
Kim, TS ;
Jung, I ;
Kim, KH ;
Heo, DS ;
Bang, YJ ;
Shin, SG ;
Kim, NK .
CANCER CHEMOTHERAPY AND PHARMACOLOGY, 1998, 41 (02) :109-116
[33]   New chiral diamines of the dioxolane series:: (+)-(4S,5S)-2,2-dimethyl-4,5-bis(diphenylaminomethyl)-1,3-dioxolane and (+)-(4S,5S)-2,2-dimethyl-4,5-bis(methyl-aminomethyl)-1,3-dioxolane [J].
Shainyan, BA ;
Nindakova, LO ;
Ustinov, MV ;
Chipanina, NN ;
Sherstyannikova, LV .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (12) :1802-1805
[34]   A phase I study of cis-malonato[(4R,5R)-4,5-bis(aminomethyl)-1,3-dioxolane] platinum(II) in patients with advanced malignancies [J].
Kim, NK ;
Kim, TY ;
Shin, SG ;
Park, YI ;
Lee, JA ;
Cho, YB ;
Kim, KH ;
Kim, DK ;
Heo, DS ;
Bang, YJ .
CANCER, 2001, 91 (08) :1549-1556
[35]   (4S,5S)-4,5-Bis(3-cyclohexyl-2-thioxobenzimidazol-1-ylmethyl)-2,2-dimethyl-1,3-dioxolane from synchrotron data [J].
Marshall, Colin ;
Harrison, William T. A. .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 :O4502-U3128
[36]   New Chiral Diamines of the Dioxolane Series: (+)-(4S,5S)-2,2-Dimethyl-4,5-bis(diphenylaminomethyl)- 1,3-dioxolane and (+)-(4S,5S)-2,2-Dimethyl-4,5-bis(methyl- aminomethyl)-1,3-dioxolane [J].
B. A. Shainyan ;
L. O. Nindakova ;
M. V. Ustinov ;
N. N. Chipanina ;
L. V. Sherstyannikova .
Russian Journal of Organic Chemistry, 2002, 38 :1802-1805
[37]   Influence of exposure and infusion times on the cytotoxicity and pharmacokinetics of cis-malonato[(4R, 5R)-4,5-bis(aminomethyl)-2-isopropyl- 1,3-dioxolane]platinum(II) [J].
Kim H.-T. ;
Kim D.-K. ;
Cho Y.-B. ;
Kim T.-S. ;
Jung I. ;
Kim K.H. ;
Heo D.S. ;
Bang Y.-J. ;
Shin S.-G. ;
Kim N.K. .
Cancer Chemotherapy and Pharmacology, 1997, 41 (2) :109-116
[38]   (-)-5-[(4R,5R)-5-(Benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]- 2,2-dimethyl-4,7-dihydro-1,3-dioxepine [J].
Carreras, Carlos R. ;
Garcia, Celina E. ;
Martin, Victor S. ;
Tonn, Carlos E. ;
Diaz Diaz, David ;
Pedro Cenal, Juan .
MOLBANK, 2010, (02) :1-3
[39]   ANTITUMOR-ACTIVITY OF CIS-MALONATO[(4R,5R)-4,5-BIS(AMINOMETHYL)-2-ISOPROPYL-1,3-DIOXOLANE]PLATINUM(II), A NEW PLATINUM ANALOG, AS AN ANTICANCER AGENT [J].
KIM, DK ;
KIM, HT ;
CHO, YB ;
TAI, JH ;
AHN, JS ;
KIM, TS ;
KIM, KH ;
HONG, WS .
CANCER CHEMOTHERAPY AND PHARMACOLOGY, 1995, 35 (05) :441-445
[40]   Pharmacokinetics of platinum following the administration of cis-(glycolato-O,O')[(4R,5R)-4,5-bis(aminomethyl) -2-isopropyl-1,3-dioxolane]platinum(II) in dogs [J].
Kim, DK ;
Kim, HT ;
Cho, YB ;
Kim, TS ;
Kim, KH ;
Hong, WS .
ANTICANCER RESEARCH, 1997, 17 (5A) :3681-3683
12345