Highly active bifunctional salenTi(Ⅳ) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN

A novel enantiopure salen ligand bearing a diphenylphosphine oxide on the 3-position of one aromatic ring was synthesized and combined with Ti(Oi-Pr)_4 as a monometallic bifunctional catalyst for asymmetric cyanosilylation reaction of aldehydes with tnmethylsilyl cyanide(TMSCN).The catalyst system e...

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Veröffentlicht in:中国化学快报:英文版 2011, Vol.22 (11), p.1285-1288
1. Verfasser: Ye Qian Wen Wei Min Ren Xiao Bing Lu
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Sprache:eng
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Zusammenfassung:A novel enantiopure salen ligand bearing a diphenylphosphine oxide on the 3-position of one aromatic ring was synthesized and combined with Ti(Oi-Pr)_4 as a monometallic bifunctional catalyst for asymmetric cyanosilylation reaction of aldehydes with tnmethylsilyl cyanide(TMSCN).The catalyst system exhibited excellent activity and moderate enantioselectivity.The addition of TMSCN to 4-nitrobenzaldehyde in the presence of 1 mol%catalyst loading could complete within 10 min at ambient temperature. An intramolecularly cooperative catalysis was observed in this system wherein the central metal Ti(Ⅳ) is suggested to play a role of Lewis acid to activate aldehydes while the appended diphenylphosphine oxide worked as Lewis base to activate TMSCN.
ISSN:1001-8417
1878-5964