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Wiley-VCH Verlag, ChemInform, 46(35), 2004

DOI: 10.1002/chin.200446029

Elsevier, Tetrahedron: Asymmetry, 13(15), p. 2085-2090

DOI: 10.1016/j.tetasy.2004.05.026

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Enantioselective Addition of Dimethylzinc to Aldehydes: Assessment of Optimal N,N-Substitution for 2-Dialkylamino-1,1,2-triphenylethanol Ligands.

This paper is available in a repository.
This paper is available in a repository.

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Abstract

A general methodology for the synthesis of 2-dialkylamino-1,1,2-triphenylethanol has been developed. Novel ligands 3, 4, and 5, bearing flexible alkyl chains on nitrogen have been synthesized by epoxide-ring opening of the encumbered (S)-triphenyl-oxirane. These ligands along with 2-piperidino-1,1,2-triphenyl ethanol 1 have been tested in the addition of dimethylzinc to alde-hydes. This allowed for the assessment of the structural features that favor the catalytic activity and selectivity of the ligands with respect to nitrogen substitution.