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Molecules 2012, 17(4), 4300-4312; doi:10.3390/molecules17044300
Article

Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans

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Received: 26 January 2012; in revised form: 19 March 2012 / Accepted: 20 March 2012 / Published: 10 April 2012
(This article belongs to the Special Issue Organocatalysis)
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Abstract: The multicomponent reaction (MCR) of aromatic aldehydes 1 and malononitrile (2) with active methylenes 5a–h in the presence of L-proline produced pyrans and thiopyrans 6a–h stereospecifically and in good yields. Moreover a novel MCR of ethyl propiolate (8) with 1 and 2 in the presence of L-proline to afford (R)-polysubstituted pyran is also reported. X-ray structures, e.e. and optical activity of the synthesized compounds indicated that L-proline as a catalyst is responsible for the observed enantioselectivity in the studied reactions.
Keywords: L-proline; pyran; assymetric synthesis; enantioselectivity; ethyl propiolate; optical activity L-proline; pyran; assymetric synthesis; enantioselectivity; ethyl propiolate; optical activity
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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MDPI and ACS Style

Elnagdi, N.M.H.; Al-Hokbany, N.S. Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans. Molecules 2012, 17, 4300-4312.

AMA Style

Elnagdi NMH, Al-Hokbany NS. Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans. Molecules. 2012; 17(4):4300-4312.

Chicago/Turabian Style

Elnagdi, Noha M. Hilmy; Al-Hokbany, Noura Saad. 2012. "Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans." Molecules 17, no. 4: 4300-4312.



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