RESUMO
A highly enantioselective cyanation of imines (up to >99 % ee) has been developed using well-designed C2 -symmetric hydrogen bonding catalysts. The catalytic strategy was characterized with low catalyst loading (0.1-1â mol %), easily accessible catalysts with diverse functional groups, and catalytic base additives. A wide range of imines, including the challenging N-Boc and N-Cbz protected ketimines and aldimines, as well as fluoroalkylated ketimines, were investigated under mild conditions to afford the products with good to excellent yields (up to 99 % yield) and high enantioselectivity (up to >99 % ee). Control experiments revealed that the multiple hydrogen bonding catalysts enhanced the reactivity and enantioselectivity of the Strecker reaction initiated by the base.
RESUMO
An enantioselective Strecker reaction to construct trifluoromethylated quaternary stereocenters with N-PMP and unexplored N-Boc trifluoromethyl ketimines catalyzed using an organophosphine dual-reagent catalyst has been developed. The enantioselectivities of the corresponding products with the same catalyst could be switched by using different N-protecting groups (N-PMP or N-Boc). The trifluoromethyl amino nitriles were obtained in high yield and high enantioselectivity in a short time and could be easily converted to a variety of useful trifluoromethyl-containing compounds.
RESUMO
A novel ratiometric and reversible chemosensor 4-((2-(Benzo[d]thiazol-2-yl)phenyl)ethynyl)-N,N-diethylaniline (BT-1) based on ortho-arylethynyl benzothiazole with large Stokes shift (Δλ≈190â¯nm) was designed and synthesized to recognize Cu2+. Copper ion induces a remarkable fluorescence enhancement and causes formation of a BT-1-Cu complex. The clamp-on coordination mode of BT-1 to Cu2+ was demonstrated using Job's plot, mass spectrum (MS) and DFT calculations. The calculations also indicate that Cu2+ was chelated to BT-1 through N and alkyne instead of S and alkyne. The probe could quantify Cu2+ with the detection limit of 3.2â¯×â¯10-9â¯M. The in vitro imaging results indicated that the probe BT-1 was membrane-permeable and could be applied into the recognition of Cu2+ ions in living cells.