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Directed Rh(I)-Catalyzed Asymmetric Hydroboration of Prochiral 1-Arylcycloprop-2-ene-1-carboxylic Acid Derivatives
Edwards, Andrew Rubina, Marina Rubin, Michael
Edwards, Andrew
Rubina, Marina
Rubin, Michael
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Abstract
A full account on rhodium-catalyzed asymmetric, directed hydroboration of functionalized prochiral cyclopropenes affording enantiomerically enriched cyclopropylboronates is reported. The scope and limitations of two alternate directing groups, ester and carboxamide, are evaluated. It was found that hydroboration of esters appeared to be more sensitive to substitution in the aromatic ring of the substrates. Specifically, ortho-halogens were detrimental for diastereo- and enantioselectivity, possibly because of additional coordination with rhodium. In contrast, more Lewis-basic amide directing groups allowed for stronger chelation to the transition metal, leading to consistently high diastereo- and enantioselectivity in hydroboration across a broader range of substrates.
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This is the peer reviewed version of the following article: A. Edwards, M. Rubina, M. Rubin, Chem. Eur. J. 2018, 24, 1394., which has been published in final form at http://doi.org/10.1002/chem.201704443. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
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2017-12-19
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Wiley
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A. Edwards, M. Rubina, M. Rubin, Chem. Eur. J. 2018, 24, 1394.