We have developed a copper/Ph-Phosferrox-catalyzed asymmetric Mannich reaction of Schiff bases with isatin-derived ketimines to prepare 3-substituted 3-aminooxindoles with excellent results.
A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to β,β-disubstituted β-fluoroacrylates catalyzed by a chiral N,O-ligand/Cu(CHCN)BF system is reported, affording chiral densely substituted pyrrolidines with four contiguous stereocenters, including one fluorinated quaternary stereocenter at the 3-position, in good to excellent yields (up to 99%), with excellent levels of diastereo- and enantioselectivities (dr >20:1; ee up to 99%).
A highly efficient asymmetric [3 + 3] annulation of ketones derived azomethine ylides with 2indolylethylenes is reported, which is achieved by catalytic Michael addition in the presence of Ag(I)/Ph-Phosferrox complex and subsequent BF 3 · Et 2 O promoted Friedel-Crafts tandem reaction in a one-pot process. This strategy addresses the challenge of selectivity between [3 + 2] cycloaddition and [3 + 3] annulation and exclusively affords a series of [3 + 3] cycloadducts, highly substituted tetrahydro-g-carbolines in excellent yields (up to 99%), with excellent levels of regioselectivities and stereoselectivities (> 20:1 rr, up to > 20:1 dr; up to 99% ee).
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