Journal
TETRAHEDRON LETTERS
Volume 51, Issue 50, Pages 6611-6614Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.10.049
Keywords
Palladium; Natural products; Heterogenous catalysis; Piperidines; Diastereoselectivity
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Funding
- Science and Technology Assistance Agency [APVV-0164-07, VMSP-P-0130-09]
- Scientific Grant Agency [VEGA 1/0340/10]
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The diastereoselective PdCl2/CuCl2-catalysed intramolecular methoxyaminocarbonylation of N-benzyl protected alkenyl amine 4 was used as a key step in the total synthesis of the naturally occurring piperidine alkaloid (-)-pinidinone. Commercially available (S)-propylene oxide was employed as starting material, delivering the key substrate 4 in three steps and 68% overall yield. Subsequently, the influence of various reaction parameters on the diastereoselectivity of the key cyclisation of 4 was scrutinised. Copper(II) chloride proved to be the optimum reagent and/or co-catalyst for the successful aminocyclisation-methoxycarbonylation tandem transformation of alkenyl amine 4 into the desired methyl esters 3 and 8. The latter were subsequently transformed into the title natural product. (C) 2010 Elsevier Ltd. All rights reserved.
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