By G. R. Stephenson, J.-P. Genet (auth.), G. R. Stephenson (eds.)
Asymmetric synthesis is among the most important strategic topics in natural chemistry, and this publication describes complicated ideas and their functions to the economic and laboratory synthesis of significant chiral molecules. The foreign workforce of hugely revered authors offer rigorous and concise reports in their components of expertise.
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16. B. Kagan and F. B. Kagan , in ref. 14, p. 203. 17. (a) N. Komatsu, M. Hashizume, T. Sugita and S. Uemura, J. Org. , 1993,58,4529; (b) N. Komatsu, M. Hashizume, T. Sugita and S. Uemur a, J . Org. , 1993, 58, 7624. 18. (a) M. Hayashi, T. Matsuda and N. Oguni, J. Chem. , Chem. , 1990, 1364; (b) M. Hayashi, T. Matsuda and N. Ogun i, J . Chem. , Perkin Trans. 1, 1992, 3135. 19. N. Iwasawa, Y. Hayashi, H. Sakurai and K. Naras aka, Chem. Lett; 1989, 1581. 20. (a) K. Mikami and M. Terada, Tetrahedron, 1992, 48, 5671; (b) M.
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. 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.
C 2. 0 @ Me • -780 C. 15 R % ee n-Pr 94 t-Bu 94 c-C6H II 92 t-Bu 91 styryl 96 I. RCHO -78°C 2. H 20 (61-87%) R % ds % ee n-Pr i-Pr vinyl 92 94 97 95 97 96 37 CH IRAL ENOLATES I. t. 2. aq. AcOH o • EIOV 3. BOC20 aq. 16 f '0 yp e ( Me ' o. _i-_Pr _2_NL _i,_E_12_0_,-_7_8°_C_ .. 2. ' 'OR* Cl 3. 4 h, -30°C - I. RCHO -78°C 2. 28 C)viJ Pr S_n-,-(O_T~f)",2,:. B-,u. 3S:. A ,-(0 :. -.. 5 h; Cool to _78°C, add RCHO stir for 20 h. 18 0 OH OR l anti 38 ADVANCED ASYMMETRIC SYNTHESIS In recent years, there has been considerable interest in the stoichiometric use of external chiral Lewis acids for mediating the asymmetric aldol reactions of ketones .