By C.H. Heathcock
Quantity 2 bargains often with the addition reactions of delocalized carbanions (enolates) and their man made family members (metalloenamines, enol ethers, allyl organometallics) with carbonyl compounds, imines and iminium ions. significant emphasis is put on C-C bond-forming reactions similar to the aldol and Mannich reactions. Acylation reactions also are incorporated during this quantity. a number of themes that experience now not formerly been reviewed are lined, together with using enzymatic aldol reactions in synthesis and the Passerini-Ugi reactions.
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Extra info for Additions to C-X &pgr;-Bonds, Part 2, Volume 2
Schade and P. von R. Schleyer, Adv. Organomet. , 1987,27, 169. 12. D. Seebach, Angew. , Int. Ed. , 1988, 27, 1624. 13. P. P. Power, Acc. Chem. , 1988, 21, 147. 14. G. Boche, Angew. , Int. Ed. , 1989,28,277; Angew. Chem.. 286. 15. E. L. Eliel, N. L. J. Angyal and G. A. Morrison, in ‘Conformational Analysis’, Wiley, New York, 1965. 16. C. H. Heathcock, in ‘Asymmetric Synthesis’, ed. J. D. Morrison, Academic Press, New York, 1984, vol. 1, pp. 155, 158. 17. While it is extremely unlikely that transition states can be easily characterized by physical measurements such as X-ray diffraction analyses, the Dunitz structure correlation principle allows a reasonable estimate to be made of the structural changes which occur along a reaction coordinate.
Lm This latter complex has often been mistaken as a geminal dianion since it frequently gives products that appear to arise from a dianion. 16' Interestingly, there are C-Li contacts in this structure and the carbanionic carbon remains tetrahedral. Carbanions of Alkali and Alkaline Earth Cations 33 The tetrahedral carbanion agrees well with the experimental results that optically active cyclopropylnitrile carbanions can undergo reprotonation with retention of configuration under certain conditions.
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Additions to C-X &pgr;-Bonds, Part 2, Volume 2 by C.H. Heathcock