期刊
ORGANIC LETTERS
卷 10, 期 19, 页码 4303-4306出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol801738d
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资金
- MEC [CTQ2006-10930/BQU]
- CAM-UCM [920234]
The cerium(IV) ammonium nitrate (CAN)-catalyzed sequential, one-pot reaction between alkylamines, beta-ketoesters, and chalcones afforded cis-4,6-disubstituted 2-alkylaminocyclohexene-1-carboxylic esters with complete diastereoselectivity. The carbon-carbon double bond of these compounds was reduced with sodium triacetoxyborohydride, again with complete diastereoselectivity. This novel two-step route allows the transformation of very simple acyclic starting materials into tetrasubstituted cyclohexane derivatives bearing four functional groups, including a cis-beta-aminoester moiety, and generates four stereocenters, three of which are adjacent and one of which is quaternary.
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