Asymmetric Synthesis - download pdf or read online

By James Morrison (Eds.)

ISBN-10: 0125077017

ISBN-13: 9780125077019

ISBN-10: 032316000X

ISBN-13: 9780323160001

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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.

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Asymmetric Synthesis by James Morrison (Eds.)


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