Download Additions to C-X &pgr;-Bonds, Part 2, Volume 2 by C.H. Heathcock PDF

By C.H. Heathcock

Quantity 2 bargains in general with the addition reactions of delocalized carbanions (enolates) and their artificial relations (metalloenamines, enol ethers, allyl organometallics) with carbonyl compounds, imines and iminium ions. significant emphasis is put on C-C bond-forming reactions comparable to the aldol and Mannich reactions. Acylation reactions also are integrated during this quantity. a number of themes that experience no longer formerly been reviewed are lined, together with using enzymatic aldol reactions in synthesis and the Passerini-Ugi reactions.

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Additional resources for Additions to C-X &pgr;-Bonds, Part 2, Volume 2

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The Corey lactone 11 is a key intermediate in the total synthesis of the physiologically active prostaglandins. It can be prepared from the lactone 10, which in turn is obtained from the bicyclic ketone 9 by reaction with m-chloroperbenzoic acid (MCPBA):4 Baeyer–Villiger Oxidation 21 As peracids are used peracetic acid, peroxytrifluoroacetic acid, m-chloroperbenzoic acid and others. Hydrogen peroxide or a peracid in combination with trifluoroacetic acid5 or certain organoselenium compounds6 have been successfully employed.

Ed. Engl. 1988, 27, 333. 8. M. J. Taschner, L. Peddada, J. Chem. , Chem. Commun. 1992, 1384–1385. 9. G. Strukul, Angew. Chem. 1998, 110, 1256–1267; Angew. Chem. Int. Ed. Engl. 1998, 37, 1198. 10. W. M. Schubert, R. R. : S. Patai), Wiley, New York, 1966, Vol. 1, p. 749–752. Bamford–Stevens Reaction Alkenes from tosylhydrazones SO2C C H N H base N SO2 C C + N2 + H CH3 CH3 1 2 p-Toluenesulfonyl hydrazones 1 (in short tosyl hydrazones) of aliphatic aldehydes or ketones furnish alkenes 2 when treated with a strong base.

Chamberlin, S. S. C. Koch, Synth. Commun. 1989, 19, 829–833. 6. L. Syper, Synthesis 1989, 167–172. 7. C. T. -C. J. Chen, Angew. Chem. 1988, 100, 342–352; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. 8. M. J. Taschner, L. Peddada, J. Chem. , Chem. Commun. 1992, 1384–1385. 9. G. Strukul, Angew. Chem. 1998, 110, 1256–1267; Angew. Chem. Int. Ed. Engl. 1998, 37, 1198. 10. W. M. Schubert, R. R. : S. Patai), Wiley, New York, 1966, Vol. 1, p. 749–752. Bamford–Stevens Reaction Alkenes from tosylhydrazones SO2C C H N H base N SO2 C C + N2 + H CH3 CH3 1 2 p-Toluenesulfonyl hydrazones 1 (in short tosyl hydrazones) of aliphatic aldehydes or ketones furnish alkenes 2 when treated with a strong base.

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