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Double-asymmetric hydrogenation strategy for the reduction of 1,1-diaryl olefins applied to an improved synthesis of CuIPhEt, a C2-symmetric N-heterocyclic carbenoid

Spahn, Elizabeth and Albright, Abigail and Shevlin, Michael and Pauli, Larissa and Pfaltz, Andreas and Gawley, Robert E.. (2013) Double-asymmetric hydrogenation strategy for the reduction of 1,1-diaryl olefins applied to an improved synthesis of CuIPhEt, a C2-symmetric N-heterocyclic carbenoid. Journal of Organic Chemistry, 78 (6). pp. 2731-2735.

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Official URL: http://edoc.unibas.ch/dok/A6212006

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Abstract

A library of iridium and rhodium phosphine catalysts have been screened for the double-asymmetric hydrogenation of 2,6-di-(1-phenylethenyl)-4-methylaniline to produce the C2-symmetric aniline precursor of the N-heterocyclic carbenoid CuIPhEt. The best catalyst produced the desired enantiomer in 98.6% selectivity. This rare example of a highly selective hydrogenation of a 1,1-diaryl olefin enables a four-step asymmetric synthesis of the C2-symmetric phenylethyl imidazolium ion (IPhEt) from p-toluidine and phenylacetylene and its conversion to the hydrosilylation catalyst CuIPhEt.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische organische Chemie (Pfaltz)
UniBasel Contributors:Pfaltz, Andreas and Pauli, Larissa
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:0022-3263
e-ISSN:1520-6904
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:10 Apr 2017 09:02
Deposited On:31 Jan 2014 09:51

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