Cyanide ion cocatalysis in Ti(salen) catalysed asymmetric cyanohydrin carbonate synthesis
- 17 March 2006
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 16,p. 1775-1777
- https://doi.org/10.1039/b602156e
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.Keywords
This publication has 19 references indexed in Scilit:
- Dual Lewis Acid−Lewis Base Activation in Enantioselective Cyanation of Aldehydes Using Acetyl Cyanide and Cyanoformate as Cyanide SourcesJournal of the American Chemical Society, 2005
- Synthetic and mechanistic studies on asymmetric cyanohydrin synthesis using a titanium(salen) bimetallic catalystTetrahedron, 2004
- Chemically Catalyzed Asymmetric Cyanohydrin SynthesesAngewandte Chemie International Edition in English, 2004
- Catalytic, Asymmetric Synthesis of Cyanohydrin Ethyl CarbonatesOrganic Letters, 2003
- Synthesis and applications of non-racemic cyanohydrinsTetrahedron: Asymmetry, 2003
- An Asymmetric Cyanation Reaction and Sequential Asymmetric Cyanation–Nitroaldol Reaction Using a [YLi3{tris(binaphthoxide)}] Single Catalyst Component: Catalyst Tuning with Achiral AdditivesAngewandte Chemie International Edition in English, 2002
- Catalytic Asymmetric Synthesis of O-Acetylcyanohydrins from Potassium Cyanide, Acetic Anhydride, and Aldehydes, Promoted by Chiral Salen Complexes of Titanium(IV) and Vanadium(V)Helvetica Chimica Acta, 2002
- A Highly Enantioselective Chiral Lewis Base-Catalyzed Asymmetric Cyanation of KetonesJournal of the American Chemical Society, 2001
- The Asymmetric Addition of Trimethylsilyl Cyanide to Aldehydes Catalyzed by Chiral (Salen)Titanium ComplexesJournal of the American Chemical Society, 1999
- TRIMETHYLSILYL CYANIDE: CYANOSILATION OF p-BENZOQUINONEOrganic Syntheses, 1981