Synthesis of a novel chiral Schiff base of ( R, R)-11,12-diamino-9,10-dihydro-9,10-ethanonanthracene and its application as ligand in Ti(IV) complex catalyzed asymmetric silylcyanation of aldehydes

A novel chiral salen ligand ( R, R)- 2 was synthesized through the condensation of ( R, R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene and 3,5-di- tert-butylsalicylaldehyde. The (salen)Ti(IV) complex formed in situ upon the treatment of ligand 2 and Ti(OPr- i) 4 was proved to be an efficient ca...

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Bibliographic Details
Published in:Catalysis communications 2007-10, Vol.8 (10), p.1443-1446
Main Authors: Zeng, Zebing, Zhao, Guofeng, Gao, Peng, Tang, Hongying, Chen, Bo, Zhou, Zhenghong, Tang, Chuchi
Format: Article
Language:English
Subjects:
Aldehydes
Asymmetric silylcyanation
Chiral (salen)Ti(IV) complex
Enantioselectivity
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Summary:A novel chiral salen ligand ( R, R)- 2 was synthesized through the condensation of ( R, R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene and 3,5-di- tert-butylsalicylaldehyde. The (salen)Ti(IV) complex formed in situ upon the treatment of ligand 2 and Ti(OPr- i) 4 was proved to be an efficient catalyst for the asymmetric trimethylsilylcyanation of aldehydes. The corresponding cyanohydrins were obtained in high yields (75–97%) with moderate to good enantioselectivities (48–76%).
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2006.12.016