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A Mild and Efficient Asymmetric Hetero-Diels-Alder Reaction of the Brassard Diene with Aldehydes

Qian Fan, Lili Lin, Jie Liu, Yaozong Huang, Xiaoming Feng*

*Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan, University, Chengdu 610064, China, Email:

Q. Fan, L. Lin, J. Liu, Y. Huang, X. Feng, Eur. J. Org. Chem., 2005, 3542-3552.

DOI: 10.1002/ejoc.200500126


A mild, enantioselective hetero-Diels-Alder (HDA) reaction of the Brassard diene with aldehydes in the presence of a chiral titanium(IV) tridentate Schiff-base complexe has been developed. The mechanism is discussed.

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Key Words

Brassard diene, Cycloaddition, Diels-Alder reaction, Schiff bases, 5,6-dihydropyran-2-ones

ID: J24-Y2005-1180