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Angewandte Chemie International Edition 12/2008; 48(1):154-6. · 13.45 Impact Factor
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ABSTRACT: The different behavior of N-tosyl imines and N-(2-pyridyl)sulfonyl imines in Cu (II)-catalyzed AFCR is described. DFT theoretical calculations on the mode of coordination of the copper atom to both types of substrates allow understanding this different reactivity.
The Journal of Organic Chemistry 08/2008; 73(16):6401-4. · 4.45 Impact Factor
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Journal of the American Chemical Society 03/2007; 129(6):1480-1. · 9.91 Impact Factor
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Angewandte Chemie International Edition 02/2007; 46(48):9257-60. · 13.45 Impact Factor
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Angewandte Chemie International Edition 02/2006; 45(4):629-33. · 13.45 Impact Factor
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ABSTRACT: [reaction: see text] The enantioselective catalytic 1,4-addition to alpha,beta-unsaturated ketimines is an unprecedented process. Herein, we document the copper-catalyzed addition of dialkylzinc reagents to (2-pyridylsulfonyl)imines of chalcones. This process occurs rapidly in the presence of a chiral phosphoramidite ligand to afford exclusively the 1,4-addition product. In the case of addition of dimethylzinc, enantioselectivities in the range 70-80% ee are obtained. The presence of the metal-coordinating 2-pyridylsulfonyl group proved to be essential for this reaction to proceed.
The Journal of Organic Chemistry 10/2005; 70(18):7451-4. · 4.45 Impact Factor
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ABSTRACT: Nanometer-sized conjugated 1,4- and 1,3,5-ethynylphenyl oligomers were synthesized starting from 3,5-di(trimethylsilylethynyl)phenylacetylene and p-[3,5-di(trimethylsilylethynyl)-1-ethynylphenyl]phenyl acetylene by cross-coupling reaction with a convenient haloaryl derivative, catalyzed by palladium(II)/copper(I), in excellent yield. The terminal acetylenes were efficiently prepared by a specific protection-deprotection methodology. All ethynylphenyl homologues obtained show fluorescence emission, with the bathochromic shift of approximately 20 nm by each ethynylphenyl unit increasing the conjugate chain. Parallel conjugated ethynylphenyl chains were prepared through the insertion of a 1,5-naphthalene subunit, and the compounds exhibit fluorescence radiation emission.
The Journal of Organic Chemistry 11/2003; 68(21):8120-8. · 4.45 Impact Factor
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Tetrahedron. 62(13):3112-3122.