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By G. R. Stephenson, J.-P. Genet (auth.), G. R. Stephenson (eds.)
Asymmetric synthesis is likely one of the most crucial strategic matters in natural chemistry, and this booklet describes complicated ideas and their purposes to the economic and laboratory synthesis of significant chiral molecules. The overseas workforce of hugely revered authors supply rigorous and concise experiences in their parts of expertise.
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30. I. ' -Q Bu-t N~ 0' : '.... ~ Et20. _lOoC. 4 h; 2. n-Bu4NF. THF R= Me~\ (97% ee), Ph~\ 0 OH II I MeO~ R (97% eel. 1b,41 Outstanding in this regard are the (S)-prolinol amides of Evans;42 these form chelated (Z)-enolates upon treatment with 2 equiv. of lithium diisopropylamide in THF at - 7S°C. 42 Significantly, the (S)-prolinol amide enolates 1. 5% HMPA; • (78-98% yld) Ratio Allyl-Br 96:4 i-Bu-! 43 Presumably, H6~ Me 1. i-Pr2NLi, TIIF, -78°C then add OBn ~ • 2. 33 this reversal of enantioselectivity reflects intermolecular chelation of the epoxide oxygen with the lithio-alkoxymethyl group, an event which would favour attack on the seemingly more hindered Re-face of the enolate.
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. In this short chapter, we attempt to summarise some of the more important developments that have occurred in chiral enolate chemistry during this period.
Grier, J . Org. , 1993, 58, 6543. 22. E. Rossiter, M. E. Hernandez and D. E. Rossiter, G. M. Swingle, M. E. G. E. Rossiter, M. Eguchi, G. M. E. Hernandez, D. Vickers, E. G. V. E. 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.
Advanced Asymmetric Synthesis by G. R. Stephenson, J.-P. Genet (auth.), G. R. Stephenson (eds.)