Issue 16, 2006
From the journal:

Chemical Communications

Cyanide ion cocatalysis in Ti(salen) catalysed asymmetric cyanohydrin carbonate synthesis†

Yuri N. Belokon,a   Eisuke Ishibashi,b   Hiroshi Nomurac  and  Michael North*b  

* Corresponding authors

a A. N. Nesmeyanov Institute of Organo-Element Compounds, Russian Academy of Sciences, Vavilov 28, Russian Federation

b School of Natural Sciences, Bedson Building, University of Newcastle, Newcastle upon Tyne, UK
E-mail: Michael.North@ncl.ac.uk

c Department of Chemistry, King's College London, Strand, London, UK

Abstract

In the presence of potassium cyanide or the potassium cyanide/18-crown-6 complex as a cocatalyst, 1–2 mol% of titanium(salen) complex 1 catalyses the asymmetric addition of achiral cyanoformates to aldehydes, giving cyanohydrin carbonates with high enantiomeric excesses; and catalyses the diastereoselective addition of chiral cyanoformates derived from α-methylbenzyl alcohol to aldehydes, a reaction which exhibits double asymmetric induction.

Graphical abstract: Cyanide ion cocatalysis in Ti(salen) catalysed asymmetric cyanohydrin carbonate synthesis

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Article information

DOI
https://doi.org/10.1039/B602156E
Article type
Communication
Submitted
14 Feb 2006
Accepted
06 Mar 2006
First published
17 Mar 2006

Chem. Commun., 2006, 1775-1777

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Cyanide ion cocatalysis in Ti(salen) catalysed asymmetric cyanohydrin carbonate synthesis

Y. N. Belokon, E. Ishibashi, H. Nomura and M. North, Chem. Commun., 2006, 1775 DOI: 10.1039/B602156E

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