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
[21]   Chiral phosphite-type ligands based on ((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) ((R,R)-TADDOL) with peripheral arylamino groups [J].
Gavrilov, K. N. ;
Maksimova, M. G. ;
Chuchelkin, I. V. ;
Lugovsky, V. V. ;
Zheglov, S. V. ;
Gavrilov, V. K. ;
Perepukhov, A. M. .
RUSSIAN CHEMICAL BULLETIN, 2017, 66 (07) :1265-1268
[22]   CRYSTAL-STRUCTURE OF (4R,5R)-2-ETHOXY-4,5-BIS[(1-METHOXY-1-PHENYL)BENZYL]-1,3-DIOXOLANE [J].
FENEAUDUPONT, J ;
DECLERCQ, JP ;
PATINY, L .
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1995, 104 (10) :623-624
[23]   Chiral phosphite-type ligands based on ((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) ((R,R)-TADDOL) with peripheral arylamino groups [J].
K. N. Gavrilov ;
M. G. Maksimova ;
I. V. Chuchelkin ;
V. V. Lugovsky ;
S. V. Zheglov ;
V. K. Gavrilov ;
A. M. Perepukhov .
Russian Chemical Bulletin, 2017, 66 :1265-1268
[24]   PHARMACOKINETICS, TISSUE DISTRIBUTION, AND EXCRETION OF CIS-MALONATO[(4R,5R)-4,5-BIS(AMINOMETHYL)-2-ISOPROPYL-1,3-DIOXOLANE]PLATINUM(II) IN DOGS [J].
CHO, YB ;
KIM, KH ;
KIM, DK .
DRUG METABOLISM AND DISPOSITION, 1995, 23 (11) :1280-1285
[25]   Enantioselective Hydrogenation over Chiral Cobalt Complexes with (+)-(1S,2S,5R)-Neomenthyldiphenylphosphine and (-)-(R,R)-2,2-Dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolane [J].
L. O. Nindakova ;
B. A. Shainyan ;
F. K. Shmidt .
Russian Journal of Organic Chemistry, 2004, 40 :973-975
[26]   Mammary excretion and placental transfer of cis-malonato[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]platinum(II) in rats [J].
Cho, YB ;
Kim, KH ;
Kim, DK ;
Miyamoto, G .
ARZNEIMITTEL-FORSCHUNG/DRUG RESEARCH, 1996, 46 (09) :926-930
[27]   Synthesis and in vitro cytotoxicity of cis-(glycolato-O,O')-[2-substituted-(4R,5R)-4,5-bis(aminomethyl)-1,3-dioxolane]platinum(II) [J].
Kim, DK ;
Gam, JS ;
Kim, HT ;
Kim, KH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (07) :771-774
[28]   Enantioselective hydrogenation over chiral cobalt complexes with (+)-(1S,2S,5R)-neomenthyldiphenylphosphine and (-)-(R,R)-2,2-dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolane [J].
Nindakova, LO ;
Shainyan, BA ;
Shmidt, FK .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (07) :973-975
[29]   SYNTHESIS OF C-14-LABELED CIS-MALONATO[(4R,5R)-4,5-BIS(AMINOMETHYL)-2-ISOPROPYL-1,3-DIOXOLANE]PLATINUM(II) (SKI 2053R) [J].
KIM, DK ;
KIM, Y ;
RIM, J ;
KIM, G ;
GAM, J ;
SONG, S ;
YOO, K ;
KIM, KH .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1994, 34 (02) :157-164
[30]   Synthesis and Characterization of (4R,5R)-1,3-dioxolance-4,5-bis(2-pyridineacrboxylic acid) [J].
姜艳 ;
卜云飞 ;
张致慧 ;
王乐勇 ;
孙小强 .
结构化学, 2011, 30 (09) :1221-1224
12345