The Journal of Organic Chemistry
NOTE
’ REFERENCES
(14) Recent examples for the synthesis of amines from imines:
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(15) 5a can be easily separated from the product mixture of 5a and
5a0 by simple recrystallization.
(16) For the synthesis of 1,2-amino alcohol by ammonolysis of
oxiranes, see: Kaburagi, Y.; Kishi, Y. Tetrahedron Lett. 2007, 48, 8967 and
references cited herein.
(2) Selected examples: (a) Billman, J. H.; Tai, K. M. J. Org. Chem.
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(3) Selected examples: (a) Orito, K.; Hatakeyama, T.; Takeo, M.;
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(b) Yi, C. S.; Lee, D. W. Organometallics 2009, 28, 947. (c) Largeron, M.;
Chiaroni, A.; Fleury, M.-B. Chem.—Eur. J. 2008, 14, 996. (d) Landge,
S. M.; Atanassova, V.; Thimmaiah, M.; Torok, B Tetrahedron Lett. 2007,
48, 5161. (e) Kodama, S.; Yoshida, J.; Nomoto, A.; Ueta, Y.; Yano, S.;
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(4) Selected examples: (a) Samec, J. S. M.; Ell, A. H.; Backvall, J.-E.
Chem.—Eur. J. 2005, 11, 2327. (b) Murahashi, S.-I.; Okano, Y.; Sato, H.;
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J.-S.; Che, C.-M. Org. Lett. 2009, 11, 4568. (d) Ell, A. H.; Samec, J. S. M.;
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Fukuda, Y.; Matsuo, J.-I. Chem. Lett. 2001, 5, 390. (g) Zhu, B.; Lazar, M.;
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(5) Selected examples: (a) Kwon, M. S.; Kim, S.; Park, S.; Bosco, W.;
Chidrala, R. K.; Park, J. J. Org. Chem. 2009, 74, 2877. (b) Kim, J. W.; He, J.;
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Cao, Y.; He, H.-Y.; Fan, K.-N. Angew. Chem., Int. Ed. 2009, 48, 4390.
(e) Kegnas, S.; Mielby, J.; Mentzel, U. V.; Christensen, C. H.; Riisager, A.
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(6) Gnanaprakasam, B.; Zhang, J.; Milsten, D. Angew. Chem., Int. Ed.
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(7) Zanardi, A.; Mata, J. A.; Peris, E. Chem.—Eur. J. 2010, 16, 10502.
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(9) (a) Huang, J.-M.; Ren, H.-R. Chem. Commun. 2010, 46, 2286.
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(10) Studies were carried out by running the reaction of benzaldehyde
and 1-bromobutane with ammonia in D2O in a NMR tube. In situ reaction
monitoring showed that imine product was formed and benzaldehyde
disappeared in the tube before the workup.
(11) (a) Hunter, D. H.; Sim, S. K. Can. J. Chem. 1972, 50, 669.
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(12) Crowell, T. I.; McLeod, R. K. J. Org. Chem. 1967, 32, 4030.
(13) General references for the synthesis of primary amines, see:
(a) Larock, R. C. Comprehensive Organic Transformations: a guide to
functional group preparation, 2nd ed.; Wiley-VCH: New York, 1999.
(b) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York,
1992; p 768 and references cited therein. (c) Collman, J. P.; Trost, B. M.;
Veroeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G.,
Stone, F. G. A., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, p 892 and
references cited therein. (d) Gibson, M. S. The Chemistry of Amino Group;
Patai, S., Ed.: Interscience: New York, 1968; p 61 and references cited therein.
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dx.doi.org/10.1021/jo102455q |J. Org. Chem. 2011, 76, 3511–3514