4542
N. J. Wallock, W. A. Donaldson / Tetrahedron Letters 43 (2002) 4541–4543
Scheme 1.
oxide gave rac-1, whose 1H and 13C NMR spectral data
5. (a) Yun, Y. K.; Donaldson, W. A. J. Am. Chem. Soc.
1997, 119, 4084–4085; (b) Godula, K.; Donaldson, W. A.
Tetrahedron Lett. 2001, 42, 153–154.
are consistent with the literature values.4d,f
In summary, the heteroatom and stereochemically rich
2-(2%-carboxycyclopropyl)glycine was prepared in ten
steps, 26% yield, from simple achiral (cyclooctatetra-
ene)Fe(CO)3. The relative stereochemistry of the three
centers is established by exo-nucleophilic attack on the
6. Brookhart, M.; Davis, E. R.; Harris, D. L. J. Am. Chem.
Soc. 1972, 94, 7853–7858.
7. Pearson, A. J.; Srinivasan, K. J. Org. Chem. 1992, 57,
3965–3973.
8. A typical experimental procedure follows: To a rapidly
stirring suspension of 5b (4.33 g, 7.65 mmol) in ether (175
mL) under N2 was added, in portions over a 24 h period,
potassium phthalimide (10.11 g, 54.6 mmol). Periodically
during this time and for an additional 6 h, the orange
ethereal mother liquors were decanted from any solid and
the reaction flask charged with additional ether (150 mL).
This was repeated until the mother liquors were colorless.
The resulting etheral layers were combined and concen-
trated to give 6b (4.81 g) as an orange solid, which was
used in the next reaction without further purification. An
analytically pure sample could be prepared by chro-
matography (SiO2, hexanes–ethyl acetate gradient=
10:14:1). Compound 6b: mp >82°C (decomposed); IR
+
(bicyclo[5.1.0]octadienyl)Fe(CO)2PPh3 cation 5b.
Acknowledgements
Financial support for this work was provided by the
National Institutes of Health (GM-42641), the Depart-
ment of Education (P200A000228) and the Marquette
University Integrative Neuroscience Research Center.
1
(KBr) 1972, 1913 cm−1; H NMR (300 MHz, CDCl3) l
References
0.52–0.61 (m, 2H), 1.06 (br pentet, J=7.9 Hz, 1H),
1.45–1.56 (m, 1H), 2.28–2.38 (m, 1H), 2.83–2.97 (m, 1H),
4.53–4.64 (m, 1H), 4.90 (br s, 1H), 5.44 (ddd, J=0.9, 3.8,
7.6 Hz, 1H), 7.34–7.40 (m, 9H), 7.41–7.50 (m, 6H), 7.66
(m, 2H), 7.78 (m, 2H); 13C NMR (75 MHz, CDCl3) l
18.10, 18.12, 19.1, 51.4, 57.0 (br), 60.2 (br), 87.0 (br) 92.2
(br), 122.7, 128.5 (d, JCP=9.2 Hz), 129.8 (d, JCP=2.0
Hz), 132.8, 133.1, 133.4 (d, JCP=10.4 Hz), 136.0 (d,
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10. A typical experimental procedure follows: To a stirring
solution of 6b (6.35 g, 10.2 mmol) in CH3CN (230 mL)
was added, in one portion, CAN (5.93 g, 10.6 mmol).
After 1 h, TLC monitoring indicated the presence of
unreacted 6b. Additional CAN (2.82 g, 5.07 mmol) was
added and the mixture was stirred for an additional 2 h.
The reaction mixture was filtered through a small bed of