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Synfacts 2008(6): 0611-0611  
DOI: 10.1055/s-2008-1078397
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

BINOL-Titanium Catalyzed Hetero-Diels-Alder Reactions

Contributor(s): Mark Lautens, Valentina Aureggi
X.-B. Yang, J. Feng, J. Zhang, N. Wang, L. Wang, J.-L. Liu, X.-Q. Yu*
Sichuan University, Chengdu and Southwest University, Chongqing, P. R. of China
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Publikationsdatum:
21. Mai 2008 (online)

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Significance

The development of an enantio­selective synthesis of 2,5-disubstituted dihydropyrones using BINOL-titanium-catalyzed hetero-Diels-Alder (HDA) reaction is reported. Aliphatic and aromatic aldehydes are both effective substrates giving the corresponding products in high yields and excellent enantioselectivities. Only a few efficient catalytic systems for hetero-Diels-Alder have been reported to date for both aromatic and aliphatic aldehydes, therefore this new system is a valuable addition. For a previous report, see: B. Gao et al. Tetrahedron 2005, 61, 5822.