A new, efficient, N-hydroxysuccinimide (NHS) mediated, mild and metal-free CDC strategy for the direct Cα-heteroarylation of diverse ethers has been developed.
A diastereoselective aminohydroxylation of olefins with a functionalized hydroxylamine is catalyzed by new iron(II) complexes. This efficient intramolecular process readily affords synthetically useful amino alcohols with excellent selectivity (dr up to > 20:1). Asymmetric catalysis with chiral iron(II) complexes and preliminary mechanistic studies reveal an iron nitrenoid is a possible intermediate that can undergo either aminohydroxylation or aziridination, and the selectivity can be controlled by careful selection of counteranion/ligand combinations.
Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an "organometallic chiron" strategy in which single enantiomers of TpMo(CO)(2)(eta(3)-pyridinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core.
"Regiodivergent catalysis" is discussed as a class of highly selective reactions of chiral substrates in racemic or enantiomerically enriched form using one or both enantiomers of a catalyst. The key point of the reactions is the highly regioselective formation of products that are constitutional isomers. The selectivity is mediated by different interactions of the enantiomerically pure catalysts with both enantiomers of the substrate. Ideally, for racemic substrates, the reactions result in highly efficient parallel resolutions and for enantiomerically pure substrates, in highly regioselective reactions for each enantiomer of the catalyst. "Regiodivergent catalysis" is highly interesting for diversity-oriented synthesis (DOS) because it provides branching points for the generation of functional and structural diversity.
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