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The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows… (More)
The intramolecular alpha-arylation of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3pi-electron radical species. These chiral SOMO-activated radical cations undergo… (More)
Ruthenium alkylidene complexes containing one aryloxide "pseudohalide" ligand catalyze ring-closing metathesis of diene and ene-yne substrates with exceptionally high efficiency. Chromatographic removal of Ru residues is unexpectedly facile, offering a convenient means of isolating pure organic products in high yields.
Singly occupied molecular orbital (SOMO) activation provides a pathway for asymmetric a-addition to aldehydes.  of a range of aldehydes. This union of organocatalysis with single-electron oxidative coupling is an intricate process involving the complex balance of catalyst, oxidant, radicophile, base, temperature, heterogeneous reaction conditions, and H… (More)
The new complex Ru(NCO)(2)(IMes)(py)(2)(=CHPh) is the first ruthenium metathesis initiator capable of fast, controlled living polymerization of functionalized norbornenes at room temperature, irrespective of monomer bulk.
Statistical mechanical averages of vectors and tensors characterizing the configurations of polypeptides have been calculated for poly-L-alanines (PLA) of xu = 2-400 peptide units. These quantities are expressed in the reference frame of the first peptide unit, the X axis being situated along the virtual bond, the Y axis in the plane of the peptide unit.… (More)
An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone… (More)
The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant… (More)