By G. R. Stephenson, J.-P. Genet (auth.), G. R. Stephenson (eds.)
Asymmetric synthesis is likely one of the most crucial strategic topics in natural chemistry, and this ebook describes complex innovations and their functions to the economic and laboratory synthesis of significant chiral molecules. The overseas group of hugely revered authors offer rigorous and concise studies in their components of expertise.
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A more accessible Lewis acid catalyst is the toluenesulfonamido (S)tryptophan oxazaborolidinone of Corey et al. 2 equiv), _78°C, 14 h, MeCH 2CN, .. 29. 86-93% ee when employed in propionitrile at - 78°C. Curiously, when used to mediate aldol additions between O-silyl ketene acetals and aldehydes, this borane catalyst leads to disappointing product ee values. A powerful approach to thioacetate aldols has been devised by Mikami et al. ). Another attractive feature of this method is that it leads to good optical yields of products even when the reactions are performed at O°C.
15 asymmetric amplification, which was discovered in the reaction of nitromethane with IX-naphthoxyacetaldehyde (49) (ligand ee: 56%; product ee: 68%), indicated the non -monomeric character of (48). '' Kobayashi et al. used chiral ytterbium and scandium catalysts in enantioselective Diels-Alder reactions'? LINEAR EFFECTS IN ENANTIOSELECTIVE SYNTHESIS 23 the metal and the presence of achiral additives. Both positive and negative deviations from linearity have been observed. 5 Asymmetric C-e bond formations: use of amino acid and peptide catalysts Although enantiomeric interactions between organic molecules have been subjects of study for a long time,31 investigations of non-linear effects in enantioselective transformations mediated (or catalysed) by purely organic compounds are still rare .
1993, 115, 10372. 30. (a) S. Kobayashi, H. Ishitani , M. Araki and I. , 1994, 35, 6325; (b) S. Kobayashi, M. Araki and I. Hachiya, J. Org. , 1994,59, 3758; (c) S. Kobayashi, H. Ishitani, I. Hachiya and M. Araki, Tetrahedron , 1994, SO, 11623; (d) S. Kobayashi, Synlett , 1994,689 (review). 31. For examples see references 1-11 in ref. 1. 32. (a) C. Agami, Bull. Soc. Chirn. ; 1988,499 (review); (b) C. Agami and C. Puchot, J. Mol . , 1986, 38, 341. 33. H. Alberts and H. Wynberg, J . Am . Chern. H.