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Synfacts 2011(10): 1134-1134  
DOI: 10.1055/s-0030-1261122
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

exo-Selective Diels-Alder Reaction of 2,4-Dienals and Nitroalkenes

Contributor(s): Benjamin List, Nathalie Dupré
Z.-J. Jia, Q. Zhou, Q.-Q. Zhou, P.-Q. Chen, Y.-C. Chen*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
20 September 2011 (online)

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exo-Selective Diels-Alder Reaction of 2,4-Dienals and NitroalkenesSynfacts 2011; 2011(12): 1385-1385
DOI: 10.1055/s-0031-1289434

Significance

Following the work of Jørgensen and co-workers on trienamine catalysis (J. Am. Chem. Soc. 2011, 133, 5053), the authors report the first asymmetric Diels-Alder reaction of 2,4-dienals and nitroalkenes catalyzed by diarylprolinol silyl ether with exclusive regioselectivity. This reaction can not succeed without judicious introduction of electron-donating substitutents on the 2,4-dienal, which raise the HOMO of the tri­eneamine intermediate. Thereby, the cyclohexene compounds are obtained with excellent er and good dr.