Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 33, Pages 10124-10129Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000284
Keywords
aldol reaction; amino acids; asymmetric catalysis; nickel; nitrogen oxides
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Funding
- National Natural Science Foundation of China [20732003, 20872097]
- PCSIRT [IRT0846]
- National Basic Research Program of China (973 Program) [2010CB833300]
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An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98%) with excellent diastereo- (up to > 99: 1 d.r.) and enantio- selectivities (up to > 99% ee). A variety of aromatic, heteroaromatic, alpha,beta-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol% L-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air- tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity.
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