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By James Morrison (Eds.)
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P. 605. Horeau, A. (1964a). J. Am. Chem. Soc. 86, 3171. Horeau, A. (1964b). Bull. Soc. Chim. , p. 2673. Horeau, A. (1969). , p. 3121. Horeau, A. (1975). Tetrahedron 3 1 , 1307. Horeau, A. (1977). In "Stereochemistry, Fundamentals and Methods" (Η. B. ). Thieme, Stuttgart. , and Nouaille, A. (1966). , p. 3953. , and Mislow, K. (1965). J. Am. Chem. Soc. 87, 4958. , Guette, J. , and Weidmann, R. (1966). Bull. Soc. Chim. , p. 3513. , and Wilen, S. H. (1981). " Wiley, New York. Kagan, Η. , and Moradpour, A.
5). A A ± H 0 2 A B + + —>A + + B+ H 0 2 A_B + —>A_ + B + The enantiomeric purity of each partially resolved ketone A is represented by an equation identical to ρ = [ A _ ] - [A ] [ A _ ] + [A ] + + = e-V - e-y 2 - (e"V + e-V The specific rotations [ a ] that are calculated by this method for various ketones are practically identical to experimental values appearing in the literature. The enantioselective rearrangement of racemic 3-methyl- and 3-ter/-butylindenes (A , R = Me and fBu) into achiral indenes (C) in the presence of an asymmetric catalyst B* (quinidine or hydroquinidine) has been analyzed in detail (Meurling and Bergson, 1974; Meurling et aL, 1976).
Even such minor solvent changes as a shift from 40 to 60% dioxane in water was shown by Tanford (1962) to cause a shift in the D-line rotation of Nacetyl-L-glutamic acid from levorotatory to dextrorotatory. In addition, Greenstein and Winitz (1961) remarked that almost all L-amino acids undergo a shift in optical rotation to more positive values when the solvent changes from water to more acidic media. The choice of a solvent for an unknown, potentially chiral molecule should be based on the observed solubility during the isolation and the potential interac tions observed in the spectral data.
Asymmetric Synthesis by James Morrison (Eds.)