Journal
CHEMICAL COMMUNICATIONS
Volume 49, Issue 38, Pages 4024-4026Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc40690c
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Funding
- National Natural Science Foundation of China [21072031, 20802009]
- Shanghai Municipal Committee of Science and Technology [10ZR1404100]
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A highly efficient cascade process of Michael-aza-Henry-hemiaminalization-dehydration was established for the construction of enantiopure tetrahydropyridines using the combination of prolinol trimethylsilyl ether and cinchona alkaloid catalysts. This new approach allowed for the application of aliphatic imines, generated in situ from aldehydes and amines. Good yields (up to 90%), high enantio- (up to >99% ee) and diastereoselectivities (>99: 1 d.r. in all cases) were achieved for a broad spectrum of substrates under mild conditions.
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