Phase transfer catalys

Keywords 2-phenylcyclohexanone, a,/ -unsaturated ketone, Michael addition, phase transfer catalys, 1,5-dicarbonyl compound... 

Montanari, F., Landini, D.,. and Rolla, F. Phase-Transfer Cataly Reactions. 101, 149-200 (1982). 

W. P. Weber andG. W. Gokel, Phase Transfer Catalysis in Organic Synthesis, Vol, 4 of Reactivity and Structure, Springer-Verlag, 1977, 250 pp. C. M. StaRKS and C. Liotta, Phase Transfer Catalysis. Academic Press, New York, 1978, 365 pp. F. MontaNaRI, D. Landini and F. Rolla, Topics in Current Chemistry 101, 149-201 (1982), E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Cataly.sis (2nd edn.), VCH Publishers, London 1983, 386 pp. T. G. Southern, Polyhedron 8, 407-13 (1989). 

Phase transfer, also called crown ether cataly, is also useful to promote the 1,4-addition of the cyanide anion to a conjugated enone. 

This reaction was carried out on cyclic and acyclic allylic carbonates. The 5-allylic thiocarbamate products were hydrolyzed to the corresponding thiol or reacted with 2-chloropyrimidine in the presence of potassium hydroxide to provide the sulfide without any loss in stereochemical purity for either example. a-Acetoxysulfones can be regarded as acid-stable, but base-labile, chiral aldehyde equivalents. These can be accessed through the palladium(0)-cataly zed reaction of geminal esters with sodium benzenesulfinate under phase-transfer conditions (eq 12). ... 

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