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Paper
Synthesis
From amide 23 (0.56 mmol scale), 24 was isolated without further
purification; yield: 90 mg (99%).
Yadav, L. D. S. RSC Adv. 2014, 4, 4181. (l) Aldoxime dehydratase:
Metzner, R.; Okazaki, S.; Asano, Y.; Gröger, H. ChemCatChem
2014, 6, 3105. (m) Ac2O, K2CO3: Song, Y.; Shen, D.; Zhang, Q.;
Chen, B.; Xu, G. Tetrahedron Lett. 2014, 55, 639. (n) Cat. (3-
FC6H4Se)2/H2O2: Yu, L.; Li, H.; Zhang, X.; Ye, J.; Liu, J.; Xu, Q.;
Lautens, M. Org. Lett. 2014, 16, 1346. (o) CBrCl3, Ph3P: Al Jasem,
Y.; Barkhad, M.; Al Khazali, M.; Butt, H. P.; El-Khwass, N. A.; Al
Azani, M.; Al Hindawi, B.; Thiemann, T. J. Chem. Res. 2014, 80.
(p) DIAD, Ph3P: Whiting, E.; Lanning, M. E.; Scheenstra, J. A.;
Fletcher, S. J. Org. Chem. 2015, 80, 1229.
HPLC: Daicel Chiralpak OJ-H column; 20 °C, 254 nm, hexane–i-PrOH
(99:1), 1 mL/min; tR = 16.6 min; >99% ee.
Spectral data for 24 were identical to those previously reported.57
Acknowledgment
This work was supported by the Canada Research Chair Program, the
Natural Sciences and Engineering Research Council of Canada, the
Canada Foundation for Innovation, Fonds de recherche du Québec –
Nature et technologies, OmegaChem, and the Université Laval.
(6) For recent selected approaches to nitriles from primary amides,
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(f) Supported vanadium catalyst: Sueoka, S.; Mitsudome, T.;
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acetamide: Enthaler, S. Chem. Eur. J. 2011, 9316. (i) Cat.
Supporting Information
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 3758–3766