Journal
CHEMCATCHEM
Volume 5, Issue 8, Pages 2405-2409Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201300215
Keywords
asymmetric catalysis; Michael addition; N,O ligands; titanium; vanadium
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Funding
- EPSRC
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Structurally well-defined bimetallic titanium(IV) (salen) and monometallic vanadium(V) (salen) complexes have been used as catalysts for the asymmetric addition of trimethylsilyl cyanide to -nitroalkenes to produce chiral nitronitriles with ee values in the range of 79-89% and conversions up to 100% at 0 degrees C. The reaction conditions (solvent, temperature, time and vanadium complex counter-ion) were optimised, and it was shown that the catalyst loading could be significantly reduced (20 to 2 mol%) and the reaction temperature increased (-40 to 0 degrees C) compared to previous studies that used an in situ prepared catalyst. The results are compared and contrasted with previous results obtained by using the same catalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes, and a transition-state structure for the asymmetric addition of trimethylsilyl cyanide to nitroalkenes is proposed to account for the observed stereochemistry.
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