Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 7, Pages 3634-3642Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00438
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- NRSC-C
- NWO-CW
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A small library of highly tunable chiral Clickphine P,N-ligands has been prepared in an enantioselective fashion by Cu-I-catalyzed asymmetric propargylic amination using a single chiral complex and a subsequent in situ cycloaddition click reaction. The scope of the propargylic amination to yield optically active triazolyl amines is described. The amines are transformed in a one-pot procedure to the corresponding Ir-Clickphine complexes, which serve as catalysts for the asymmetric hydrogenation of di-, tri-, and tetrasubstituted unfunctionalized alkenes. Enantioselectivities of up to 90% ee were obtained in these hydrogenations, which are among the best reported in the case of the tetrasubstituted substrate 2-(4 '-methoxyphenyl)-3-methylbut-2-ene (9) (87% ee). This is a demonstration of the effective use of the chiral pool, as from one chiral catalyst a library of chiral Ir complexes has been synthesized that can hydrogenate various alkenes with high selectivity.
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