Phase transfer catalysis reviews

M. J. O Donnell, Asymmetric PTC Reactions. Part 1 Amino Acids , Phases - The Sachem Phase Transfer Catalysis Review 1998, Issue 4, pp. 5-8. 

For general reviews on asymmetric phase-transfer catalysis, see (a) Shioiri, T. (1997) Handbook of Phase-Transfer Catalysis (eds Y. Sasson and R. Neumann), Blackie Academic Professional, London, Chapter 14 (b) O Donnell, M.J. (1998) Phases - The Sachem Phase Transfer Catalysis Review, (4) p. 5 (c) O Donnell, M.J. (1999) Phases - The Sachem Phase Transfer Catalysis Review, (5) p. 5 ... 

Makosza, M., Fedorynski, M. (1998) Allqflation of phenylacetonitrile. The Sachem Phase Transfer Catalysis Review, Sachem Inc. 1998, Issue 3, 2. 

A mixture of (R)-2-octyl methanesulfonate, KCI, Iricaprylmethylammonium diloride, and water stirred and heated 1.5 hrs. at 100° (+)-(S)-2-dilorooctane. Y 74% optical purity 89.2%. Also bromides and fluorides, iodides with race-mization, and f. phase transfer catalysts, s. D. Landini, S. Quid, and F. Rolla, Synthesis 1975, 430 phase transfer catalysis, review, s. M. M kosza, Pure Appl. Chem. 43, 439 (1975). 

For a review of this type of phase-transfer catalysis, see Liotta, C. in Patai, Ref. 363, p. 157. 

For reviews of phase-transfer catalysis of this reaction, see Starks, C.M. Liotta, C. Ref. 437, p. 140 Weber, W.P. Gokel, G.W. Phase Transfer Catalysis in Organic Synthesis, Ref. 437, p. 85. 

For reviews, see E. V. Dehmlow, Angew. Chem. Int. Ed. Engl., 16, 493 (1977) W. P. Weber and G. W. Gokel, Phase Transfer Catalysis in Organic Synthesis, Springer-Verlag, Berlin, 1977. 

Pletcher has reviewed papers on indirect electrosynthesis when phase transfer catalysis is used to allow the chemical step to occur homogeneously in an organic solvent immiscible with the aqueous electrolyte [10,127],... 

There are many examples on the asymmetric phase transfer catalysis, but highly efficient ones are not so many though they are increasing in recent years.17-101 This review will highlight the notable examples with emphasis on recent reports. 

The term phase transfer catalysis is also spelled as phase-transfer catalysis. In this review, we will adopt the former without hyphen. PTC means both phase transfer catalysis and phase transfer catalyst To avoid the confusion, full spellings will be adopted. 

A large number of reviews of phase-transfer catalysis in general, incorporating the use of quaternary ammonium salts, have appeal ed since the 1960s [e.g. 18, 51-66]. Many of the early articles are of important historical interest, whereas the later reviews illustrate the manner in which applications of the technique have mush-... 

Since 1971 phase transfer catalysis has emerged as a broadly useful tool(9-16). not only in organic chemistry, but also in inorganic chemistry(17), for new analytical applications(18), in electrochemistry(27a), photochemistry(27b), and especially in polymer chemistry.(21.27-31) The substantial number of publications, patents, reviews, and books (200 to 400 per year since 1980) concerned with PTC in both scientific and commercial applications attests to the high level of interest that this technique has generated. 

Phase transfer catalysis (1,2) has become in recent years a widely used, well-established synthetic technique applied with advantage to a multitude of organic transformations. In addition to a steadily increasing number of reports in the primary literature, there are several reviews (3-6), comprehensive monographs (7-10) and an ACS Audio Course (1 ) which describe the phase transfer process and which provide extensive compilations of phase transfer agents and reaction types. While the list of applications and in many cases the synthetic results are impressive, phase transfer catalysts (PTCs) suffer some of the same disadvantages as more conventional hetero-and homogeneous catalysts — separation and... 

There has been a useful review of phase-transfer catalysis in nucleophilic aromatic substimtion. A comparison has been reported of the reactions with nucleophiles of l-chloro-2,4-dinitrobenzene (substimtion) and 4-nitrophenyl diphenyl phosphate (dephosphorylation) in neutral micelles of dodecyl (10) and (23) polyoxyethylene glycol. In the substimtion reaction considerable amounts of ether may be formed by reaction with alkoxide ions at the micellar surface. Differences in reactivity of the two substrates are probably due to differences in their location in the micellar structures. ... 

To facilitate accesses to suitably functionalized sialic acid derivatives and complex sialyloligosaccharides for other usehil neoglycoconjugates, phase transfer catalysis (PTC) has been exploited extensively [for reviews see 42]. This process provided a wide range of carbohydrate derivatives under essentially clean Sn2 transformations. In the case of acetochloroneuraminic acid 1, the PTC reactions always provided inverted a-sialic acid derivatives [43]. para-Formylphenyl sialoside 7 [44], together with many other sialoside derivatives such as 8-10 [43], including thioacetate 12 [45] and azide 14 [46], were thus obtained (Scheme 1). Aldehyde 7 and similar glycosides are of particular interest since they could be directly conjugated to protein by reductive amina-tion after suitable deprotection [44]. 

For reviews, see Starks Liotta, Ref. 404, pp. 128-138 Weber Gokel Phase Transfer Catalysis in Organic Synthesis, Ref. 404, pp. 73-84. For the use of phase transfer catalysis to convert, selectively, one OFI group of a diol or triol to an ether, see de la Zerda Barak Sasson Tetrahedron 1989, 45, 1533. 

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