Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 11, Pages 2228-2232Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800243
Keywords
Asymmetric hydrogenation; -Alkynyl imines; Hydrazones; Chemoselective; Enantioselective
Categories
Funding
- National Natural Science Foundation of China [21572131, 21620102003]
- Shanghai Municipal Education Commission [201701070002E00030]
- Science and Technology Commission of Shanghai Municipality [15JC1402200]
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As an update of our continuous interest in the hydrogenation of hydrazones, a chemo- and enantioselective hydrogenation of alkynyl-aryl hydrazones was developed using a rhodium complex [Rh((R,Sp)-JosiPhos)(cod)]SbF6 as the catalyst and benzoic acid as an additive. Directed by a p-nitrobenzamido group, the chiral propargyl hydrazines, which can be easily converted to chiral propargylamines of significant importance and potential use, were obtained with good yields, excellent chemoselectivities and good to excellent enantioselectivities. Although the enantioselectivity of the reaction and the substrate/catalyst ratio require further refinement, the reported methodology provides an alternative route for the efficient preparation of chiral propargylamines.
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