Journal
ORGANIC LETTERS
Volume 16, Issue 3, Pages 752-755Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol403463h
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Funding
- National Natural Science Foundation of China [21072031, 21342009]
- China Postdoctoral Science Foundation [2013M531111]
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A four-component asymmetric alpha-aminoxylation/aza-Michael/Mannich cascade reaction for the construction of fully substituted chiral tetrahydro-1,2-oxazine derivatives was accomplished in high yields with excellent enantio- and diastereoselectivities under mild conditions. The 1,2-oxazine derivative could be transformed to the corresponding multifunctional chiral amino alcohol by N-O cleavage and fused-tricyclic 4-amino-substituted tetrahydroquinolines in good yields with excellent stereoselectivities followed by a Friedel-Crafts reaction. Also a 4-alkoxy-substituted tetrahydroquinoline was achieved by C-4 inversion of a 4-amino-substituted tetrahydroquinoline.
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