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Molecules 2011, 16(6), 5298-5314; doi:10.3390/molecules16065298
Article

Enantio and Diastereoselective Addition of Phenylacetylene to Racemic α-chloroketones

, , , ,  and *
Alma Mater Studiorum, Dipartimento di Chimica “G: Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy
* Author to whom correspondence should be addressed.
Received: 26 May 2011 / Revised: 17 June 2011 / Accepted: 22 June 2011 / Published: 23 June 2011
(This article belongs to the Special Issue Catalytic Asymmetric Synthesis)
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Abstract

In this report, we have presented the first diastereoselective addition of phenylacetylene to chiral racemic chloroketones. The addition is controlled by the reactivity of the chloroketones that allowed the stereoselective reaction to be performed at –20 °C. Chiral racemic chloroketones are used in the reaction. By carefully controlling the temperature and the reaction time we were able to isolate the corresponding products in moderate yields and with good, simple and predictable facial stereoselection. Our reaction is a rare example of the use of chiral ketones in an enantioselective alkynylation reaction and opens new perspectives for the formation of chiral quaternary stereocenters.
Keywords: alkynylation; (R,R)-salen; chloroketones; Me2Zn; phenylacetylene alkynylation; (R,R)-salen; chloroketones; Me2Zn; phenylacetylene
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Alesi, S.; Emer, E.; Capdevila, M.G.; Petruzziello, D.; Gualandi, A.; Cozzi, P.G. Enantio and Diastereoselective Addition of Phenylacetylene to Racemic α-chloroketones. Molecules 2011, 16, 5298-5314.

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