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 e-book describes complicated innovations and their purposes to the economic and laboratory synthesis of vital chiral molecules. The overseas group of hugely revered authors supply rigorous and concise experiences in their parts of expertise.
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Oppolzer et al. 38). 39), which I. n-BuLi, THF, -78°C; then R-HaI, HMPA; 2. LiOH, HZOz,aq. 38 .. 98-99% de 49 CHIRAL ENOLATES I. 5 N aq. HCl; 3. 39 allows access to a wide variety of a-amino acids in high enantiomeric purity after alkylation and removal ofthe chiral auxiliary. Remarkably, these glycine enolates are of sufficient nucleophilicity to even readily displace secondary alkyl iodides. 5o,51 The N -deprotection step is generally accomplished by mild acid hydrolysis, the bornyl-1O,2-sultam being detached afterwards by the standard saponification method.
Mol . , 1986, 38, 341. 33. H. Alberts and H. Wynberg, J . Am . Chern. H. Alberts and H. Wynberg, J. Chern. , Chern. , 1990, 453. 34. (a) Z. R. N. Jacobsen , J. Am. Chern. , 1993, 115, 5326; (b) B. Schmidt and D. Seebach, Angew. , 1991, 103, 1383; Angew . Chern. Int . Ed. , 1991,30,1321. J. HALE and S. 1 Introduction For more than half a century, organic chemists have sought to control the stereochemistry of reactions involving chiral enolates for the purpose of constructing single diastereoisomers of molecules in enantiomerically pure form; yet, it is only since the early 1980s that significant progress has been made on this topic.
12). 4). Asymmetric amplification was only achieved with chiralligands of relatively high optical purity. As a result of negative deviations, use of (37) with low ee gave almost racemic muscone. * See also Chapter 11. 4 Non-linear effects in the muscone synthesis" % ee of chiral ligand % ee of muscone % yield of muscone 100 100 93 76 33 89 75 82 77 96 80 60 50 40 26 20 93 6 The non-linear effects were suggested to arise from differences in chemical behaviour of diastereomeric dinuclear copper complexes.