CHAPTER 5: Interconversion and Analysis of Stereoisomers

Enhanced diagrams for many of the structures / schemes / figures are given below:

Scheme 5.1


5.1	5.3	enantiomer of 5.1

Scheme 5.2


5.4	achiral enol	achiral enol	enantiomer of 5.4

Scheme 5.3


5.5	achiral endiolate	5.6

Figure 5.1: Reaction Pathway / Energy Diagrams for the Reprotonation of a: Enediolate 5.3 and b: Enediolate 5.7.

Scheme 5.4


5.8	5.9

Structure 5.10

for clarity, the ammonium ions are not shown

Scheme 5.7

Figure 5.2: Energy / Reaction Pathway Diagram for Kinetic Resolution using a Chiral Reagent.

Figure 5.3: Energy / Reaction Pathway Diagram for Kinetic Resolution using an Achiral Reagent and a Chiral Catalyst.

Figure 5.4: Interaction of Enantiomers with a Chiral Stationary Phase Containing a: Two and b: Three Binding Sites.

Scheme 5.17

Figure 5.6: a: The Methyl Ester Region of the 1H NMR Spectra of Racemic 5.29 in the Presence of Increasing Amounts of Chiral Shift Reagent 5.28. b: The Methyl Ester Region of the NMR spectra of Racemic (Bottom) and Enantiomerically Pure (Top) Samples of 5.29 in the Presence of 40 mol % of Shift Reagent 5.28.

Scheme 5.19


5.32 (R)-enantiomer	(R)-Mosher's acid chloride	5.33a


5.32 (S)-enantiomer		5.33b

Figure 5.7: Extract of the 1H NMR Spectrum of Compound 5.33 Obtained from a: Racemic 5.32 and b: 5.32 with an Enantiomeric Excess of 59%.

Structures 5.32 and 5.34

Figure 5.8: The ORD Curves Obtained for Epoxides 5.34 and 5.35.


5.34R	5.34S	5.35

Structures 5.39 and 5.40


5.39	5.40

Figure 5.9: ORD Traces for the Diastereomeric Ketones 5.41 and 5.42.


5.41	5.42

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