Journal of the American Chemical Society
Communication
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ASSOCIATED CONTENT
* Supporting Information
Representative experimental procedures and necessary charac-
terization data for all new compounds are provided. This material
■
S
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
(11) Giani, R.; Marinone, E.; Melillo, G.; Borsa, M.; Tonon, G. C.
Arzneim.-Forsch. 1988, 38, 1139.
ACKNOWLEDGMENTS
■
The National Institutes of Health (NIH) is greatly appreciated
for providing financial support (2R01GM068433). C.W. thanks
the Alexander von Humboldt Foundation for his postdoctoral
fellowship. We would also like to thank Dr. Antoni Jurkiewicz,
Dr. Ian Steele, and Dr. Jin Qin for their expertise in NMR-
spectroscopy, X-ray crystallography, and mass spectrometry,
respectively.
(12) For examples on regioselective ring opening of epoxides without
directing groups using amines as nucleophiles, see: (a) Sekar, G.; Sing,
V. K. J. Org. Chem. 1999, 64, 287. (b) Rampalli, S.; Chaudhari, S. S.;
Akamanchi, K. G. Synthesis 2000, 32, 78. (c) Rodríguez, J. R.; Navarro, A.
Tetrahedron Lett. 2004, 45, 7495. (d) Sundararajan, G.; Vijayakrishna,
K.; Varghese, B. Tetrahedron Lett. 2004, 45, 8253. (e) Chakraborti, A. K.;
Kondaskar, A.; Rudrawar, S. Tetrahedron 2004, 60, 9085. (f) Bartoli, G.;
Bosco, M.; Carlone, A.; Locatelli, M.; Massaccesi, M.; Melchiorre, P.;
Sambri, L. Org. Lett. 2004, 6, 2173. (g) Williams, D. B. G.; Lawton, M.
Tetrahedron Lett. 2006, 47, 6557. (h) Shivani; Pujala, B.; Chakraborti, A.
K. J. Org. Chem. 2007, 72, 3713. (i) Robinson, M. W. C.; Timms, D. A.;
Williams, S. M.; Graham, A. E. Tetrahedron Lett. 2007, 48, 6249. (j) Arai,
K.; Lucarini, S.; Salter, M. M.; Ohta, K.; Yamashita, Y.; Kobayashi, S. J.
Am. Chem. Soc. 2007, 129, 8103. (k) Procopio, A.; Gaspari, M.; Nardi,
M.; Oliverio, M.; Rosati, O. Tetrahedron Lett. 2008, 49, 2289. (l) Chimni,
S. S.; Bala, N.; Dixit, V. A.; Bharatam, P. V. Tetrahedron 2010, 66, 3042.
(m) Pathare, S. P.; Akamanchi, K. G. Tetrahedron Lett. 2013, 54, 6455.
(13) For examples on regioselective ring-opening of epoxides without
directing groups using alcohols or phenols as nucleophiles, see: (a) Iida,
T.; Yamamoto, N.; Matsunaga, S.; Woo, H.-G.; Shibasaki, M. Angew.
Chem., Int. Ed. 1998, 37, 2223. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl,
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(16) The relative configurations of 3l (CCDC-999510) and 4s
(CCDC-999511) were assigned to be erythro unambiguously by X-ray
crystal structure analysis (Supporting Information (SI), p 23). The
supplementary crystallographic data can be obtained free of charge from
data_request/cif. The erythro configuration of 3l was confirmed by
NOESY-measurements on its oxazolidine derivative 10 (SI, pp 20−21
and 137−139). The other ring-opening products were assigned by
analogy assuming a common SN2-type reaction pathway.
́
̀
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