Journal
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
Volume 37, Issue 4, Pages 571-575Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/bkcs.10728
Keywords
Ethyl acetoacetate; Stereoselective -aminoallylation; (S)-tert-Butanesulfinamide; Cross-metathesis; (-)-Pinidinone
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Funding
- Priority Research Centers Program through the National Research Foundation of Korea (NRF) - Ministry of Education, Science and Technology [NRF-2009-0094071]
- Hallym University Research Fund [HRF-201506-004]
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An expeditious stereoselective synthesis of a naturally occurring 2,6-disubstituted piperidine alkaloid, (-)-pinidinone, has been accomplished with an overall yield of 31% in total eight steps. The synthesis involves ethyl acetoacetate as the starting material and the stereoselective -aminoallylation of aldehyde with (S)-tert-butanesulfinamide, allyl bromide, and indium and Grubbs' olefin cross-metathesis as the pivotal steps.
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