2005
DOI: 10.1002/chin.200511044
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Effective Activation of the Chiral Salen/Ti(OiPr)4 Catalyst with Achiral Phenolic N-Oxides as Additives in the Enantioselective Cyanosilylation of Ketones.

Abstract: The activation of chiral titanium(IV) complexes with phenolic N-oxides additives has been found to provide an alternative strategy for the asymmetric cyanosilylation of ketones. By using 10 mol % of chiral salen−titanium(IV) complex in combination with 1 mol % achiral phenolic N-oxide as an additive, aromatic, aliphatic and heterocyclic ketones have been converted into the corresponding cyanohydrin trimethylsilyl

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“…The purified products were liquids and characterized by 1 H and 13 C NMR and were in agreement with the reported values. 22,23 Characterization Data 2-Phenyl-2-(trimethylsilyloxy)propanenitrile ( Table 3, Entry 1). 1…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…The purified products were liquids and characterized by 1 H and 13 C NMR and were in agreement with the reported values. 22,23 Characterization Data 2-Phenyl-2-(trimethylsilyloxy)propanenitrile ( Table 3, Entry 1). 1…”
Section: Methodsmentioning
confidence: 99%
“…Enantiomerically pure cyanohydrins are important structural units, which can easily be converted into variety of organic intermediates including a-hydroxy acids, a-amino acids, and b-amino alcohols. [1][2][3][4][5][6][7][8] Significant advances have been made for developing efficient catalysts for the synthesis of chiral cyanohydrins [9][10][11][12] using Snapper and Hoveyda's peptide-Al catalysts, 13 Jacobsen's thiourea catalysts, 14 Feng's double-activation, [15][16][17][18][19][20][21][22][23] amino acid salt, 24 and Deng's chiral Lewis base. 25,26 Besides, in search of new methodology, Belokon and North have reported bimetallic Ti(IV) salen complex 27 while Shibasaki and coworkers have used bifunctional catalysts with Ti(IV), 28,29 Gd(O i Pr) 3 , 30 and Sm(O i Pr) 3 31 for the enantioselective cyanosilylation of ketones.…”
Section: Introductionmentioning
confidence: 99%