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Synthesis 2011(12): 1840-1846  
DOI: 10.1055/s-0030-1260020
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 4-Hydroxy-4H-chromenes by Reaction of Salicylic Aldehydes with Alkynals Catalyzed by Silyl Prolinol Ethers

José Alemán*, Cuauhtémoc Alvarado, Vanesa Marcos, Alberto Núñez, José Luis García Ruano*
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
Fax: +34(914)973966; e-Mail: jose.aleman@uam.es; e-Mail: joseluis.garcia.ruano@uam.es;
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Publikationsverlauf

Received 25 January 2011
Publikationsdatum:
28. April 2011 (online)

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Abstract

We report an oxa-Michael/Baylis-Hillman tandem reaction between salicylaldehydes and alk-2-ynals activated by silyl prolinol ethers, affording 2,3-disubstituted 4-hydroxy-4H-chromenes in good yields and enantiomeric ratios (up to 98:2).

Key words

organocatalysis - proline - chromenes - asymmetric synthesis - aminocatalysis

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15

To our surprise, the authors (ref. 5d) indicate that in their hands reactions with salicylaldehyde were unsuccessful, despite the fact that they used very similar conditions to those used in the reactions described in this work.

16

CCDC 808683 (5a) contains the supplementary crystallographic data. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033,
e-mail: deposit@ccdc.cam.ac.uk].