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Synfacts 2007(2): 0229-0229  
DOI: 10.1055/s-2006-955770
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Addition of TMSCN to Aldehydes Catalyzed by a Polymeric V-Salen Complex

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
N. H. Khan*, S. Agrawal, R. I. Kureshy, S. H. R. Abdi, V. J. Mayani, R. V. Jasra
Central Salt and Marine Chemicals Research Institute, Bhavnagar, India
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

Chiral polymeric vanadium(V) salen complex 4 was prepared and used as a chiral cata­lyst in the asymmetric addition of trimethylsilyl cyanide (TMSCN) to aldehydes. The polymeric salen ligand 3 was prepared by the polymerization of (1R,2R)-diaminocyclohexane 1 with 3,3′-methyl­enebis[5-tert-butyl-6-hydroxybenzaldehyde] 2 (eq. 1). The reaction of ligand 3 with vanadyl sulfate hydrate gave the polymeric vanadium salen complex 4 (eq. 2). The asymmetric addition of TMSCN to a variety of aldehydes 5 took place in the presence of polymeric vanadium salen complex 4 to give the adducts 6 in 76-99% conversion with 77-96% ee (eq. 3).