Journal of Organic Chemistry p. 535 - 542 (2018)
Update date:2022-08-18
Topics:
Harkiss, Alexander H.
Sutherland, Andrew
A synthetic route to cis-2-methyl-4-oxo-6-alkylpiperidines has been developed using a 6-endo-trig cyclization of (E)-enones. The base-mediated intramolecular cyclization was found to be general for both alkyl- and aryl-substituted enones, providing the corresponding 4-oxopiperidines in high yields (80-89%). Stereoselective reduction of the 2,6-cis-disubstituted 4-oxopiperidines then gave the 2,4,6-cis,cis-trisubstituted 4-hydroxypiperidines in high diastereoselectivity. The general nature of this approach was demonstrated with the synthesis of the natural products, spruce alkaloid and (+)-241D.
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Doi:10.1021/ja00200a016
(1989)Doi:10.1021/ja01617a042
(1955)Doi:10.1006/jcat.2000.2950
(2000)Doi:10.1016/j.tetlet.2013.03.066
(2013)Doi:10.1002/anie.201409990
(2015)Doi:10.1021/jo01035a002
(1964)