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Figure 18. 1 H NMR spectrum of (3S) citronellyl pivalate in CDCl 326
Figure 19. GC/MS trace of [(3S,6RS)-6,7-epoxycitronellyl pivalate] + [(3S)citronellyl pivalate] co-injection (gradient 150 °C → 230 °C, ∆T = 5 °C/min)27
Page 1: ABSTRACTASYMMETRIC SYNTHESIS OF 6,7
Page 4 and 5: NOTE:THIS PAGE IS OPTIONAL, AND REQ
Page 6 and 7: APPROVEDFor the Department of Chemi
Page 8 and 9: ACKNOWLEDGMENTSI would like to than
Page 10 and 11: FigureLIST OF FIGURESPage1. Califor
Page 12 and 13: 37.38.39.ix13 C NMR Spectrum of (3S
Page 14 and 15: 2support the contention that the fe
Page 16 and 17: Figure 2. California Red Scale pher
Page 18 and 19: 6creation of the chiral center at C
Page 20 and 21: 8During the early 1990s Professor E
Page 22 and 23: 10across the top of the molecule, a
Page 24 and 25: 12molecule and also shows that the
Page 26 and 27: 14Figure 10. (R,R) Jacobsen’s cat
Page 28 and 29: 16stereoselectivity. With tri-subst
Page 30 and 31: 18physical properties (except optic
Page 32 and 33: 20Calo in 1990 published a method o
Page 34 and 35: 22halide into an excess of magnesiu
Page 36 and 37: RESULTS AND DISCUSSIONSynthesis of
Page 40 and 41: Figure 20. GC/MS trace of (3S) citr
Page 42 and 43: Figure 22. 1 H NMR spectrum of (3S,
Page 44 and 45: 32IR spectroscopy .Separation of Ep
Page 46 and 47: Figure 25. GC/MS trace of (3S,6RS)-
Page 52 and 53: 40due to the starting material (3S)
Page 54 and 55: 42Figure 33. 1 H NMR spectrum of (3
Page 56 and 57: Figure 36. 13 C NMR spectrum of (3S
Page 58 and 59: 46Figure 37. 13 C NMR Spectrum of (
Page 60 and 61: 48major peak by GC/MS (Figure 40).
Page 62 and 63: Figure 42. Results of GC/MS library
Page 64 and 65: 52GC/MS trace showed that only inte
Page 66 and 67: EXPERIMENTALAll 1 H Nuclear Magneti
Page 68 and 69: 56Synthesis of (3S,6RS)-6,7-Epoxyci
Page 70 and 71: 58catalyst in the product. Another
Page 72 and 73: 60was observed and no temperature c
Page 74 and 75: REFERENCES1. Bodenheimer, F.S. Citr

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