Journal
TETRAHEDRON LETTERS
Volume 61, Issue 44, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.152405
Keywords
Alkaloids; Diastereoselective substitution; Enamine; Iminium; Zinc complexes
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In the presence of ZnCl2, chiral protected amino-ketones and amino-aldehydes gave zinc enamino-complexes. Both enamine and iminium structures of these complexes were observed in H-1 and C-13 NMR spectra depending on the solvent. Introduction of either an allyl or a hydrogen substituent was performed using allylmagnesium chloride or NaBH4 in excess leading to various heterocycles. With the aminoketones diastereoselectivity (de = 50) was observed respectively. Homoconiine and coniine precursors were prepared by this strategy. (C) 2020 Elsevier Ltd. All rights reserved.
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