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Synthesis 2009(12): 2089-2100  
DOI: 10.1055/s-0029-1216826
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Tunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers

Craig R. Smith, Hwan Jung Lim, Aibin Zhang, T. V. RajanBabu*
Department of Chemistry, The Ohio State University, 100 W. 18th Ave, Columbus, OH 43210, USA
Fax: +1(614)2921685; e-Mail: rajanbabu.1@osu.edu;
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Publikationsverlauf

Received 20 April 2009
Publikationsdatum:
14. Mai 2009 (online)

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Abstract

α-Alkylstyrenes undergo efficient hydrovinylation (addition of ethene) in the presence of a nickel catalyst prepared from [(allyl)NiBr]2, Na+[BAr4]- [Ar = 3,5-bis(trifluoromethyl)phenyl], and a phosphoramidite ligand giving products in excellent yields and enantioselectivities. In many cases phosphoramidites derived from achiral 2,2′-biphenol are almost as good as ligands derived from the more expensive enantiopure 1,1′-bi(2-naphthol)s. The hydrovinylation products, which carry two versatile latent functionalities, an aryl and a vinyl group, are potentially useful for the synthesis of several important natural products containing benzylic all-carbon quaternary centers.

Key words

alkenes - asymmetric catalysis - hydrovinylation - phosphoramidite ligands - nickel

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For the use of phosphoramidites derived from bis-phenols of spirobisindane in related asymmetric hydrovinylations, see reference 6.

23

Details of the synthesis of these compounds will be reported separately.

25

Biphenol-derived phosphoramidites have been used with excellent results in copper-catalyzed conjugate additions: see ref. 4c.