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In search of enantioselective catalysts for the Henry reaction : are two metal centers better than one?

Constable, Edwin C. and Zhang, Guoqi and Housecroft, C and Neuburger, Markus and Schaffner, Silvia and Woggon, Wolf-D.. (2009) In search of enantioselective catalysts for the Henry reaction : are two metal centers better than one? New Journal of Chemistry, 33 (5). pp. 1064-1069.

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Official URL: http://edoc.unibas.ch/dok/A5260120

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Abstract

Catalysts for the asym. Henry reaction involving Cu(II) complexes of the chiral Schiff bases N,N'-(1R,2R)-(-)-1,2-cyclohexylenebis(3-hydroxysalicylideneamine) (H21) and N,N'-(1R,2R)-(-)-1,2-cyclohexylenebis(3-ethoxysalicylideneamine) (H22), and (H23), which is the reduced analog of H21, were studied.  Whereas [Cu(1)] and [Cu(2)] give poor yields and enantioselectivity, [Cu(3)] produced moderate to high yields and enantioselectivities were optimal when reactions were carried out in toluene rather than a polar solvent.  A significant finding is that both yield and enantioselectivity are enhanced when a 2nd equiv. of Cu(OAc)2 is added to the catalyst.  The single-crystal structures of [Cu(3)] and [Cu(1)(H2O)] are presented, and the host-guest interactions and mol. packing in the latter are compared with those in [Cu(2)(H2O)].
Faculties and Departments:05 Faculty of Science
05 Faculty of Science > Departement Chemie > Chemie
05 Faculty of Science > Departement Chemie > Chemie > Anorganische Chemie (Constable)
UniBasel Contributors:Woggon, Wolf-Dietrich and Constable, Edwin Charles
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:1144-0546
e-ISSN:1369-9261
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:08 May 2017 08:32
Deposited On:22 Mar 2012 13:46

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