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	赵立文刘继冯宇何艳梅范青华
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 01.09.2012 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Subjects	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 POLYMERS codendrimer amino acid chiral diphosphine PHOSPHINES ENHANCEMENT COMPLEXES SUPPORTS DENDRITIC BINAP LIGANDS asymmetric catalysis ASYMMETRIC HYDROGENATION hydrogenation
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ISSN	1001-604X 1614-7065
DOI	10.1002/cjoc.201200648

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Summary:	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.
Bibliography:	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
ISSN:	1001-604X 1614-7065
DOI:	10.1002/cjoc.201200648