Enantioselective iridium-catalyzed allylic amination of ammonia and convenient ammonia surrogates |
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Authors: | Pouy Mark J Leitner Andreas Weix Daniel J Ueno Satoshi Hartwig John F |
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Affiliation: | Department of Chemistry, University of Illinois, 600 South Matthews Avenue, Urbana, Illinois 61801, USA. |
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Abstract: | Iridium-catalyzed, asymmetric allylation of ammonia as a nucleophile occurs with stereoselectivity to form a symmetric diallylamine, and related allylation of the inexpensive ammonia equivalent potassium trifluoroacetamide or the highly reactive ammonia equivalent lithium di-tert-butyliminodicarboxylate forms a range of conveniently protected, primary, alpha-branched allylic amines in high yields, high branched-to-linear regioselectivities, and high enantiomeric excess. The reactions of ammonia equivalents were conducted with a catalyst generated from a phosphoramidite containing a single stereochemical element. |
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