Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 33, Pages 11505-11512Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201905263
Keywords
chemoselectivity; enantioselectivity; homogeneous catalysis; hydrogenation
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Funding
- National Natural Science Foundation of China [21572131, 21620102003, 21831005, 91856106] Funding Source: Medline
- Shanghai Municipal Education Commission [201701070002E00030] Funding Source: Medline
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In order to effectively synthesize chiral alpha-amino aldehydes, which have a wide range of potential applications in organic synthesis and medicinal chemistry, a highly chemo- and enantioselective hydrogenation of alpha-formyl enamides has been developed, catalyzed by a rhodium complex of a P-stereogenic bisphosphine ligand. Under different hydrogen pressures, the chiral alpha-amido aldehydes and beta-amido alcohols were obtained in high yields (97-99 %) and with excellent chemo- and enantioselectivities (up to >99.9 % ee). The hydrogenation can be carried out on a gram scale and with a high substrate/catalyst ratio (up to 20 000 S/C), and the hydrogenated products were further converted into several important chiral products. Computations of the catalytic cycle gave a clear description for the R/S pathways, provided a reasonable explanation for the enantioselectivity, and revealed several other specific features.
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