107-69-7Relevant articles and documents
Iridium-Catalyzed Amidation of in Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters
Chang, Sukbok,Gwon, Yunyeong,Kim, Dongwook,Lee, Minhan
supporting information, p. 1088 - 1093 (2022/02/10)
Disclosed herein is a convenient Ir-catalyzed amidation of esters to access α-amido esters. Initially prepared silyl ketene acetals are directly employed, without separate purification, for subsequent amidation with an oxycarbonylnitrenoid precursor using the Cp*(LX)Ir(III) catalyst. The α-amidation was facile for both α-aryl and α-alkyl esters. Density functional theory studies revealed that the generation of a putative Ir-nitrenoid is facilitated by the chelation of the countercation additive during the N-O bond cleavage of the nitrene precursor.
Copper-catalyzed oxidative benzylic C(sp3)-H amination: Direct synthesis of benzylic carbamates
Liu, Shuai,Achou, Rapha?l,Boulanger, Coline,Pawar, Govind,Kumar, Nivesh,Lusseau, Jonathan,Robert, Frédéric,Landais, Yannick
supporting information, p. 13013 - 13016 (2020/11/05)
A new efficient strategy to access benzylic carbamates through C-H activation is reported. The use of a catalytic amount of a Cu(i)/diimine ligand in combination with NFSI ((PhSO2)2NF) or F-TEDA-PF6 as oxidants and H2NCO2R as an amine source directly leads to the C-N bond formation at the benzylic position. The mild reaction conditions and the broad substrate scope make this transformation a useful method for the late-stage incorporation of a ubiquitous carbamate fragment onto hydrocarbons. This journal is
Direct, intermodular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines
Weix, Daniel J.,Markovic, Dean,Ueda, Mitsuhiro,Hartwig, John F.
supporting information; experimental part, p. 2944 - 2947 (2009/12/05)
The direct reaction between carbamates and achiral allylic carbonates to form branched, conveniently protected primary allylic amines with high regioseiectivity and enantioselectivity Is reported. This process occurs without base or with 0.5 equiv K3PO4 In the presence of a metalacyclic iridium catalyst containing a labile ethylene ligand. The reactions of aryl-, heteroaryl-, and alkyl-substituted allylic carbonates with BocNH 2, FmocNH2, CbZNH2, TrocNH2, TeocNH2, and 2-oxazolidinone occur In good yields, with high selectivity for the branched isomer and high enantioselectivities (98% average ee).