D. Ma, Y. Jiang / Tetrahedron: Asymmetry 11 (2000) 3727–3736
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(s, 3H), 1.3–1.2 (m, 12H); MS m/z 450 (M++H+), 376, 350, 334, 244, 105, 77, 57, 41; anal. calcd
for C27H31NO5: C, 72.14; H, 6.95; N, 3.12; found: C, 72.03; H, 6.98; N, 3.03.
3.2.8. (1S,2R,3R)-2-Benzoyl-3-[(R)-((3-((2,2-dimethyl-1-oxo)propyl)-2,2-dimethyl)-4-oxazol-
idinyl)]-cyclopropyl phenyl ketone 7d and (1S,2S,3R)-2-benzoyl-3-[(R)-((3-((2,2-dimethyl-
1-oxo)propyl)-2,2-dimethyl)-4-oxazolidinyl)]-cyclopropyl phenyl ketone 8d
1H NMR (300 MHz, CDCl3) l 8.05–7.95 (m, 4H), 7.61–7.55 (m, 2H), 7.45–7.35 (m, 4H),
4.15–4.05 (m, 2H), 3.95–3.90 (m, 1H), 3.71–3.65 (m, 1H), 2.85 (m, 1H), 2.65 (m, 1H), 1.65 (s,
3H), 1.52 (s, 9H), 1.41 (s, 3H); MS m/z 450 (M++H+), 434, 376, 350, 334, 244, 105, 77, 57, 41;
anal. calcd for C27H31NO5: C, 72.14, H, 6.95, N, 3.12; found: C, 71.88; H, 7.00; N, 3.11.
3.2.9. (1R,2R,3R)-2-Benzoyl-3-[(R)-((3-((2,2-dimethyl-1-oxo)propyl)-2,2-dimethyl)-4-oxazol-
idinyl)]-cyclopropanecarboxylic acid, morpholino amide 6e
1
[h]2D0=−12.3 (c 2.0, CHCl3); H NMR (300 MHz, CDCl3) l 8.0 (d, J=7.5 Hz, 2H), 7.55 (t,
J=7.4 Hz, 1H), 7.42 (t, J=7.7 Hz, 2H), 4.1 (m, 1H), 4.0 (m, 1H), 3.91–3.75 (m, 3H), 3.71–3.52
(m, 6H), 3.42 (t, J=4.6 Hz, 1H), 2.72–2.68 (dd, J=9.1, 4.4 Hz, 1H), 2.15 (dt, J=9.2, 5.2 Hz,
1H), 1.5 (s, 3H), 1.41 (s, 9H), 1.37 (s, 3H); MS m/z 459 (M++H+), 359, 343, 253, 105, 57; anal.
calcd for C25H34N2O6: C, 65.48; H, 7.47; N, 6.11; found: C, 65.21; H, 7.46; N, 5.82.
3.2.10. (1S,2R,3R)-2-Benzoyl-3-[(R)-((3-((2,2-dimethyl-1-oxo)propyl)-2,2-dimethyl)-4-oxazol-
idinyl)]-cyclopropane-carboxylic acid, morpholino amide 7e and (1S,2S,3R)-2-benzoyl-3-
[(R)-((3-((2,2-dimethyl-1-oxo)propyl)-2,2-dimethyl)-4-oxazolidinyl)]-cyclopropanecarboxylic
acid, morpholino amide 8e
1H NMR (300 MHz, CDCl3) l 8.05 (d, J=7.3 Hz, 2H), 7.55 (m, 1H), 7.48 (t, J=7.4 Hz, 2H),
4.08 (m, 1H), 4.01–3.92 (m, 1H), 3.88 (m, 1H), 3.55–3.45 (m, 8H), 2.93–2.75 (m, 2H), 2.65–2.47
(m, 1H), 1.69 (s, 3H), 1.62 (s, 3H), 1.52 (s, 9H); MS m/z 459 (M++H+), 359, 345, 256, 105, 57;
anal. calcd for C25H34N2O6: C, 65.48; H, 7.47; N, 6.11; found: C, 65.49; H, 7.73; N, 6.10.
3.2.11. (1R,2R,3R)-2-Acetyl-3-[(R)-((3-((2,2-dimethyl-1-oxo)propyl)-2,2-dimethyl)-4-oxazol-
idinyl)]-cyclopropanecarboxylic acid, ethyl ester 6f
1
[h]2D0=−30.7 (c 1.6, CHCl3); H NMR (300 MHz, CDCl3) l 4.25–4.13 (m, 2H), 4.09–3.95 (m,
2H), 3.82 (m, 1H), 2.45 (m, 2H), 2.2 (s, 3H), 1.95 (dd, J=13.4, 8.2 Hz, 1H), 1.58 (s, 3H), 1.5
(s, 3H), 1.4 (s, 9H), 1.25 (t, J=7.1 Hz, 3H); MS m/z 356 (M++H+), 256, 254, 240, 194, 57, 43;
anal. calcd for C18H29NO6: C, 60.83; H, 8.22; N, 3.94; found: C, 61.25; H, 8.43; N, 3.90.
3.2.12. (1S,2R,3R)-2-Acetyl-3-[(R)-((3-((2,2-dimethyl-1-oxo)propyl)-2,2-dimethyl)-4-oxazol-
idinyl)]-cyclopropanecarboxylic acid, ethyl ester 7f and (1S,2R,3R)-2-acetyl-3-[(R)-((3-((2,2-
dimethyl-1-oxo)propyl)-2,2-dimethyl)-4-oxazolidinyl)]-cyclopropane-carboxylic acid, ethyl ester 8f
1H NMR (300 MHz, CDCl3) l 4.15–4.09 (m, 3H), 3.97 (m, 1H), 3.81 (m, 1H), 2.65–2.30 (m,
2H), 2.25 (s, 3H), 2.18 (m, 1H), 1.69–1.47 (m, 15H), 1.24 (m, 3H); MS m/z 340 (M+−CH3), 282,
240, 194, 57, 43; anal. calcd for C18H29NO6: C, 60.83; H, 8.22; N, 3.94; found: C, 60.86; H, 8.35;
N, 3.29.
3.2.13. (1R,2R,3R)-2-Acetyl-3-[(R)-((3-((2,2-dimethyl-1-oxo)propyl)-2,2-dimethyl)-4-oxazol-
idinyl)]-cyclopropanecarboxylic acid, tert-butyl ester 6g
[h]2D0=−60.6 (c 1.0, CHCl3); H NMR (300 MHz, CDCl3) l 4.15 (m, 1H), 3.82–3.75 (m, 1H),
1
2.45–2.38 (m, 2H), 2.3 (s, 3H), 2.10 (m, 1H), 1.52–1.41 (m, 24H); MS m/z 384 (M++H+), 328,