Next Article in Journal
Study of the Extraction Process and In Vivo Inhibitory Effect of Ganoderma Triterpenes in Oral Mucosa Cancer
Next Article in Special Issue
Enantioselective Addition of Allyltin Reagents to Amino Aldehydes Catalyzed with Bis(oxazolinyl)phenylrhodium(III) Aqua Complexes
Previous Article in Journal
The Main Anticancer Bullets of the Chinese Medicinal Herb, Thunder God Vine
Previous Article in Special Issue
Ru/Me-BIPAM-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes and α-Ketoesters
Molecules 2011, 16(6), 5298-5314; doi:10.3390/molecules16065298
Article

Enantio and Diastereoselective Addition of Phenylacetylene to Racemic α-chloroketones

, , , ,  and *
Received: 26 May 2011; in revised form: 17 June 2011 / Accepted: 22 June 2011 / Published: 23 June 2011
(This article belongs to the Special Issue Catalytic Asymmetric Synthesis)
Download PDF [235 KB, uploaded 18 June 2014]
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.

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

Alesi S, Emer E, Capdevila MG, Petruzziello D, Gualandi A, Cozzi PG. Enantio and Diastereoselective Addition of Phenylacetylene to Racemic α-chloroketones. Molecules. 2011; 16(6):5298-5314.

Chicago/Turabian Style

Alesi, Silvia; Emer, Enrico; Capdevila, Montse Guiteras; Petruzziello, Diego; Gualandi, Andrea; Cozzi, Pier Giorgio. 2011. "Enantio and Diastereoselective Addition of Phenylacetylene to Racemic α-chloroketones." Molecules 16, no. 6: 5298-5314.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert