Facile Synthesis of Chiral Diphosphine-Containing Multiple Dendrimeric Catalysts for Enantioselective Hydrogenation
A new kind of chiral diphosphine PyrPhos-functionalized codendrimers have been synthesized via a liq- uid-phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent pre- cipitation without the need for chromatographic separation, and well characterized...
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| Published in | Chinese journal of chemistry Vol. 30; no. 9; pp. 2009 - 2015 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.09.2012
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1001-604X 1614-7065 |
| DOI | 10.1002/cjoc.201200648 |
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| Abstract | A new kind of chiral diphosphine PyrPhos-functionalized codendrimers have been synthesized via a liq- uid-phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent pre- cipitation without the need for chromatographic separation, and well characterized by 1H, 13C and 31p NMR, MALDI-TOF mass spectroscopy as well as elemental analysis. Their rhodium complexes were applied to the asymmetric hydrogenation of a-acetamido cinnamic acids. Excellent enantioselectivities were achieved, which are comparable to those with the corresponding small molecular catalysts. In addition, these codendrimeric catalysts showed better catalytic performance than the dendrimeric catalysts with Rh（PyrPhos） sites located in the focal point ofpoly（aryl ether） dendrons or in the periphery ofpoly（propyleneimine） dendrimers. |
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| AbstractList | A new kind of chiral diphosphine PyrPhos‐functionalized codendrimers have been synthesized via a liquid‐phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent precipitation without the need for chromatographic separation, and well characterized by
1
H,
13
C and
31
P NMR, MALDI‐TOF mass spectroscopy as well as elemental analysis. Their rhodium complexes were applied to the asymmetric hydrogenation of
α
‐acetamido cinnamic acids. Excellent enantioselectivities were achieved, which are comparable to those with the corresponding small molecular catalysts. In addition, these codendrimeric catalysts showed better catalytic performance than the dendrimeric catalysts with Rh(PyrPhos) sites located in the focal point of poly(aryl ether) dendrons or in the periphery of poly(propyleneimine) dendrimers. A new kind of chiral diphosphine PyrPhos‐functionalized codendrimers have been synthesized via a liquid‐phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent precipitation without the need for chromatographic separation, and well characterized by 1H, 13C and 31P NMR, MALDI‐TOF mass spectroscopy as well as elemental analysis. Their rhodium complexes were applied to the asymmetric hydrogenation of α‐acetamido cinnamic acids. Excellent enantioselectivities were achieved, which are comparable to those with the corresponding small molecular catalysts. In addition, these codendrimeric catalysts showed better catalytic performance than the dendrimeric catalysts with Rh(PyrPhos) sites located in the focal point of poly(aryl ether) dendrons or in the periphery of poly(propyleneimine) dendrimers. A new kind of codendrimers with multiple PyrPhos moieties in the periphery was synthesized via a liquid‐phase organic synthesis strategy, and proved to be very effective in the Rh‐catalyzed asymmetric hydrogenation of prochiral olefins. A new kind of chiral diphosphine PyrPhos-functionalized codendrimers have been synthesized via a liquid-phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent precipitation without the need for chromatographic separation, and well characterized by 1H, 13C and 31P NMR, MALDI-TOF mass spectroscopy as well as elemental analysis. Their rhodium complexes were applied to the asymmetric hydrogenation of a-acetamido cinnamic acids. Excellent enantioselectivities were achieved, which are comparable to those with the corresponding small molecular catalysts. In addition, these codendrimeric catalysts showed better catalytic performance than the dendrimeric catalysts with Rh(PyrPhos) sites located in the focal point of poly(aryl ether) dendrons or in the periphery of poly(propyleneimine) dendrimers. A new kind of chiral diphosphine PyrPhos-functionalized codendrimers have been synthesized via a liquid-phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent precipitation without the need for chromatographic separation, and well characterized by 1H, 13C and 31P NMR, MALDI-TOF mass spectroscopy as well as elemental analysis. Their rhodium complexes were applied to the asymmetric hydrogenation of [alpha]-acetamido cinnamic acids. Excellent enantioselectivities were achieved, which are comparable to those with the corresponding small molecular catalysts. In addition, these codendrimeric catalysts showed better catalytic performance than the dendrimeric catalysts with Rh(PyrPhos) sites located in the focal point of poly(aryl ether) dendrons or in the periphery of poly(propyleneimine) dendrimers. A new kind of chiral diphosphine PyrPhos-functionalized codendrimers have been synthesized via a liq- uid-phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent pre- cipitation without the need for chromatographic separation, and well characterized by 1H, 13C and 31p NMR, MALDI-TOF mass spectroscopy as well as elemental analysis. Their rhodium complexes were applied to the asymmetric hydrogenation of a-acetamido cinnamic acids. Excellent enantioselectivities were achieved, which are comparable to those with the corresponding small molecular catalysts. In addition, these codendrimeric catalysts showed better catalytic performance than the dendrimeric catalysts with Rh（PyrPhos） sites located in the focal point ofpoly（aryl ether） dendrons or in the periphery ofpoly（propyleneimine） dendrimers. |
| Author | Liu, Ji He, Yanmei Zhao, Liwen Fan, Qinghua Feng, Yu |
| AuthorAffiliation | Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences （ CAS）, Beoing 100190, China |
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| Keywords | POLYMERS codendrimer amino acid chiral diphosphine PHOSPHINES ENHANCEMENT COMPLEXES SUPPORTS DENDRITIC BINAP LIGANDS asymmetric catalysis ASYMMETRIC HYDROGENATION hydrogenation |
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| Notes | 31-1547/O6 asymmetric catalysis, codendrimer, chiral diphosphine, hydrogenation, amino acid A new kind of chiral diphosphine PyrPhos-functionalized codendrimers have been synthesized via a liq- uid-phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent pre- cipitation without the need for chromatographic separation, and well characterized by 1H, 13C and 31p NMR, MALDI-TOF mass spectroscopy as well as elemental analysis. Their rhodium complexes were applied to the asymmetric hydrogenation of a-acetamido cinnamic acids. Excellent enantioselectivities were achieved, which are comparable to those with the corresponding small molecular catalysts. In addition, these codendrimeric catalysts showed better catalytic performance than the dendrimeric catalysts with Rh（PyrPhos） sites located in the focal point ofpoly（aryl ether） dendrons or in the periphery ofpoly（propyleneimine） dendrimers. ArticleID:CJOC201200648 istex:4B9A8B41297AA54724CE0AB02FFFD2971788A8E6 the National Basic Research Program of China (973 Program) - No. 2010CB833300 and 2011CB808600 ark:/67375/WNG-SZ56LM71-B ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 |
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| References_xml | – reference: Wang, Z. J.; Deng, G. J.; Li, Y.; He, Y. M.; Tang, W. J.; Fan, Q. H.. Org. Lett., 2007, 9, 1243. – reference: Chen, Y. C.; Wu, T. F.; Jiang, L.; Deng, J. G.; Liu, H.; Zhu, J.; Jiang, Y. Z.. J. Org. Chem., 2005, 70, 1006. – reference: Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G.. Chem. Ber., 1986, 119, 3326. – reference: Liu, J.; Feng, Y.; He, Y. M.; Yang, N. F.; Fan, Q. H.. New J. Chem., 2012, 36, 380. – reference: Kassube, J. K.; Gade, L. H.. Top. Organomet. Chem., 2006, 20, 61. – reference: Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J.. J. Am. Chem. Soc., 1993, 115, 11496. – reference: van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H.. Chem. Rev., 2002, 102, 3717. – reference: Feng, Y.; He, Y. M.; Zhao, L. W.; Huang, Y. Y.; Fan, Q. H.. Org. Lett., 2007, 9, 2261. – reference: Deng, G. J.; Fan, Q. H.; Chen, X. M.. Chin. J. Chem., 2002, 20, 1139. – reference: Fan, Q. H.; Chen, Y. M.; Chen, X. M.; Jiang, D. 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| Snippet | A new kind of chiral diphosphine PyrPhos-functionalized codendrimers have been synthesized via a liq- uid-phase strategy in high yields. The resulting... A new kind of chiral diphosphine PyrPhos‐functionalized codendrimers have been synthesized via a liquid‐phase strategy in high yields. The resulting... A new kind of chiral diphosphine PyrPhos-functionalized codendrimers have been synthesized via a liquid-phase strategy in high yields. The resulting... |
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| SubjectTerms | amino acid asymmetric catalysis Chemistry Chemistry, Multidisciplinary chiral diphosphine codendrimer Hydrogenation Mass spectroscopy Physical Sciences Rhodium Science & Technology TOF质谱 不对称氢化反应 乙酰氨基肉桂酸 催化剂 加氢反应 合成 手性双膦 树枝状 |
| Title | Facile Synthesis of Chiral Diphosphine-Containing Multiple Dendrimeric Catalysts for Enantioselective Hydrogenation |
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