By G. R. Stephenson, J.-P. Genet (auth.), G. R. Stephenson (eds.)
Asymmetric synthesis is without doubt one of the most crucial strategic topics in natural chemistry, and this ebook describes complex suggestions and their functions to the commercial and laboratory synthesis of vital chiral molecules. The foreign staff of hugely revered authors offer rigorous and concise studies 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.
1 preparation, their excellent diastereofacial selectivity and the ease with which the au xiliary can be removed and recycled. 2). " Changing the counterion from boron to lithium generally leads to a drop in diastereoselectivity along with the formation of enantiomeric products. " The stereoselectivity of both these processes is presumably the result of bidentate metal chelation to the oxazolidinone carbonyl and the enolate oxygen. 8 Depending on the precise enolisation conditions OH 0 0 0 r R~N~O ~e ~e syn, syn 000 HN~O Me Me r:' Bn OH Sn(OTlh Et3N • CH2CI2• _78°C (Q EtNM~ 0 Bn 0 0 R~N~O Me Me anti.
M. Swingle,Chem. , 1992,92,771 (review). 23. K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki and A. Watanabe, J. Chem. , Chem. , 1991, 1632. 24. -L. Zhou and A. Pfaltz, Tetrahedron, 1994, SO, 4467; (b) G. van Kot en, Pure Appl. , 1994,66, 1455. 25. e. Bolm, M. Ewald and M. Felder, Chem. ; 1992, 125, 1205; (b) e. Bo1m, Tetrahedron: Asymmetry, 1991,2, 701. 26. A. L. M. A. L. Feringa , Tetrahedron, 1994, SO, 4479. 27. e. Bolm, M. Felder and 1. Muller, Synlett , 1992,439. 28. A. G. R. R. Muci, J. Am. Chem.
Advanced Asymmetric Synthesis by G. R. Stephenson, J.-P. Genet (auth.), G. R. Stephenson (eds.)