30543-90-9Relevant academic research and scientific papers
Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates
Qian, Deyun,Bera, Srikrishna,Hu, Xile
supporting information, p. 1959 - 1967 (2021/02/06)
Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enecarbamates (N-Cbz-protected enamines) and alkyl halides with high regio- and enantioselectivity. The method works for both nonactivated and activated alkyl halides and is able to produce enantiomerically enriched amines with two minimally differentiated α-alkyl substituents. The mild conditions lead to high functional group tolerance, which is demonstrated in the postproduct functionalization of many natural products and drug molecules, as well as the synthesis of chiral building blocks and key intermediates to bioactive compounds.
Enantioselective conjugate addition of nitroalkanes to vinyl sulfone: An organocatalytic access to chiral amines
Zhu, Qiang,Lu, Yixin
supporting information; experimental part, p. 1721 - 1724 (2009/09/08)
Organocatalytic asymmetric conjugate addition of nitroalkanes to vinyl sulfone mediated by cinchona alkaloid-derived thiourea catalyst afforded the desired Michael product with good enantioselectivity. The described method, in combination with ready desul
Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol
Campbell, Matthew J.,Johnson, Jeffrey S.
, p. 1521 - 1524 (2008/02/02)
Equation Presented An SN2 mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxyamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.
Amination of Grignard reagents with retention of configuration
Hoffmann, Reinhard W.,Hoelzer, Bettina,Knopff, Oliver
, p. 1945 - 1947 (2007/10/03)
(formula presented) The stereochemistry of electrophilic amination has been probed using the chiral Grignard reagent 5, in which the magnesium-bearing carbon atom is the sole stereogenic center. Amination with azidomethyl phenyl sulfide 1 and with 0-sulfonyloxime 2 were found to proceed with full retention of configuration.
