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Synthesis of Vicinal Dimethyl Chirons by Asymmetric Hydrogenation of Trisubstituted Alkenes

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Department of Chemistry, Texas A&M University, College Station, Texas 77840
[email protected]
Cite this: J. Am. Chem. Soc. 2009, 131, 37, 13236–13237
Publication Date (Web):August 31, 2009
https://doi.org/10.1021/ja905458n
Copyright © 2009 American Chemical Society
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    Abstract

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    Roche ester derivatives were converted to trisubstituted alkenes with allylic chiral centers. Hydrogenation of these substrates with chiral analogues of Crabtree’s catalyst, specifically, an optically active carbene oxazoline derivative, were found to be mostly catalyst controlled. However, the peripheral functionalities and protecting groups had significant effects and could be adjusted to give high stereoselectivities. The upshot of this work is that α,ω-functionalized chirons to introduce 1,2-dimethyl functionalities into acyclic chains have been developed.

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