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7 J. S. Baum, D. A. Shook, H. M. L. Davies and D. H. Smith, Synth.
Commun., 1987, 17, 1709–1716.
8 We have tentatively assigned the product of this reaction sequence to be:
and tolerates a wide range of alcohols. In addition, amines can be
used as substrates for the amidation with 4, thus providing access
to a-diazo-b-ketoamides. The use of diazo ketoacids as coupling
partners in various synthetic efforts is currently being employed in
our laboratory.
The authors gratefully acknowledge the NSF (predoctoral
fellowship for E.M.F.), Bristol-Myers Squibb (Graduate
Fellowship in Synthetic Organic Chemistry to E.M.F.),
AstraZeneca, Boehringer Ingelheim, Johnson & Johnson, Pfizer,
Merck, Amgen, Research Corporation, Roche, the Dreyfus
Foundation, and GlaxoSmithKline for generous funding.
.
Notes and references
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Catalytic Methods for Organic Synthesis with Diazo Compounds from
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9 A similar transesterification on a 2u alcohol was recently described, see:
J. Lim, D.-J. Choo and Y. H. Kim, Chem. Commun., 2000, 553–554.
10 When alcohol 5 was subjected to the identical reaction conditions, the
only isolated product arose from a Wolff Rearrangement of 3, followed
by addition of 5 into the resulting ketene to provide ii
2 For a recent review of C–H activation using diazo compounds, see:
H. M. L. Davies and R. E. J. Beckwith, Chem. Rev., 2003, 103,
2861–2904.
3 For recent examples of Wolff rearrangements, see: (a) R. Sarpong,
J. T. Su and B. M. Stoltz, J. Am. Chem. Soc., 2003, 125, 13624–13625;
(b) H. Yang, K. Foster, C. R. J. Stephenson, W. Brown and E. Roberts,
Org. Lett., 2000, 2, 2177–2179; (c) R. R. Julian, J. A. May, B. M. Stoltz
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4 For a review of cyclopropanation, see: H. Lebel, J.-F. Marcoux,
C. Molinaro and A. B. Charette, Chem. Rev., 2003, 103, 977–1050.
5 For selected examples, see: (a) S. Kitagaki, M. Anada, O. Kataoka,
K. Matsuno, C. Umeda, N. Watanabe and S.-I. Hashimoto,
J. Am. Chem. Soc., 1999, 121, 1417–1418; (b) J. A. May and
B. M. Stoltz, J. Am. Chem. Soc., 2002, 124, 12426–12427; (c)
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and H.-J. Dietrich, J. Am. Chem. Soc., 1999, 121, 1748–1749; (d)
A. Padwa, M. A. Brodney, J. P. Marino, Jr., M. H. Osterhout and
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.
11 F. Kido, K. Yamaji, T. Abiko and M. Kato, J. Chem. Res. (S), 1993,
18–19.
12 For a typical hydrogenolysis, see Supporting Information.
13 For a typical esterification procedure, see Supporting Information.
14 It is known that a-diazoacetoacetates can be converted to a-diazoace-
tates under basic conditions. For a general procedure, see: M. P. Doyle,
R. E. Austin, A. S. Bailey, M. P. Dwyer, A. B. Dyatkin, A. V. Kalinin,
M. M. Y. Kwan, S. Liras, C. J. Oalmann and R. J. Pieters, et al.,
J. Am. Chem. Soc., 1995, 117, 5763–5775.
15 For examples of a-diazo-b-ketoamides, see: (a) A. Padwa and L. Zhi,
J. Am. Chem. Soc., 1990, 112, 2037–2038; (b) A. Jeganathan,
S. K. Richardson, R. S. Mani, B. E. Haley and D. S. Watt,
J. Org. Chem., 1986, 51, 5362–5367; (c) A. Padwa, D. C. Dean,
D. J. Fairfax and S. L. Xu, J. Org. Chem., 1993, 58, 4646–4655.
6 (a) A. Padwa, D. J. Austin and S. F. Hornbukle, J. Org. Chem., 1996,
61, 63–72; (b) C. H. Yoon, M. J. Zaworotko, B. Moulton and
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