Enantioselective iridium-catalyzed allylic amination of ammonia and convenient ammonia surrogates.
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.
Pouy
Mark J
MJ
Department of Chemistry, University of Illinois, 600 South Matthews Avenue, Urbana, Illinois 61801, USA.
Leitner
Andreas
A
Weix
Daniel J
DJ
Ueno
Satoshi
S
Hartwig
John F
JF