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2 reacted with pinacol (chloromethyl)boronate in acetonitrile at 80°C to give N-linked (formamidomethyl)-boronate. Versleijen, J. P. G.; Faber, P. M.; Bodewes, H. H.; Braker, A. H.; van Leusen, D.; van Leusen, A. M. Tetrahedron Lett. 1995, 36, 2109.
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0029079223
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N-Metalated carbamates are uncommon nucleophiles. There is no precedent report on tert-butyl carbamate, but recently CBZ-carbamate has been used as a nucleophile. Mjalli, A. M. M.; Chapman, K. T.; Zhao, J.; T., N. A.; Peterson, E. P.; MacCoss, M. Bioorg. Med. Chem. Lett. 1995, 5, 1405.
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19
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3342923002
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note
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The structure of 4 was determined by a 2D NMR experiment in which the cross peak between NH and BCH in the Cosy45 spectrum was identified.
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20
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3342973412
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note
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Boronate 4 was readily purified by "flash chromatography" on silica gel. However, the longer residence time (>45 min) on silica gel resulted in hydrolysis of boronate 4 to boronic acid. Fortunately, the boronic acid can be completely recovered by elution of the silica gel column with pinanediol to obtain pinanediol boronic ester.
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0001175929
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Other examples of in-situ generation and capture of reactive anions by boronic esters: (a) Sadhu, K. M.; Maltesen, D. S. Organometalics 1985, 4, 1687. (b) Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795. (c) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150. (d) Brown, H. C.; Phadke, A. S.; Rangaishenvi, M. V. J. Am. Chem. Soc. 1988, 110, 6263. (e) Michnik, T. J.; Matteson, D. S. Synlett 1991, 631. (f) Wallace, R., II; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941.
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Sadhu, K.M.1
Maltesen, D.S.2
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0001207083
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Other examples of in-situ generation and capture of reactive anions by boronic esters: (a) Sadhu, K. M.; Maltesen, D. S. Organometalics 1985, 4, 1687. (b) Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795. (c) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150. (d) Brown, H. C.; Phadke, A. S.; Rangaishenvi, M. V. J. Am. Chem. Soc. 1988, 110, 6263. (e) Michnik, T. J.; Matteson, D. S. Synlett 1991, 631. (f) Wallace, R., II; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941.
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Sadhu, K.M.1
Matteson, D.S.2
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0000253386
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Other examples of in-situ generation and capture of reactive anions by boronic esters: (a) Sadhu, K. M.; Maltesen, D. S. Organometalics 1985, 4, 1687. (b) Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795. (c) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150. (d) Brown, H. C.; Phadke, A. S.; Rangaishenvi, M. V. J. Am. Chem. Soc. 1988, 110, 6263. (e) Michnik, T. J.; Matteson, D. S. Synlett 1991, 631. (f) Wallace, R., II; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941.
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24
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0000871060
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Other examples of in-situ generation and capture of reactive anions by boronic esters: (a) Sadhu, K. M.; Maltesen, D. S. Organometalics 1985, 4, 1687. (b) Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795. (c) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150. (d) Brown, H. C.; Phadke, A. S.; Rangaishenvi, M. V. J. Am. Chem. Soc. 1988, 110, 6263. (e) Michnik, T. J.; Matteson, D. S. Synlett 1991, 631. (f) Wallace, R., II; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941.
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Brown, H.C.1
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Rangaishenvi, M.V.3
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25
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85093511443
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Other examples of in-situ generation and capture of reactive anions by boronic esters: (a) Sadhu, K. M.; Maltesen, D. S. Organometalics 1985, 4, 1687. (b) Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795. (c) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150. (d) Brown, H. C.; Phadke, A. S.; Rangaishenvi, M. V. J. Am. Chem. Soc. 1988, 110, 6263. (e) Michnik, T. J.; Matteson, D. S. Synlett 1991, 631. (f) Wallace, R., II; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941.
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Matteson, D.S.2
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Other examples of in-situ generation and capture of reactive anions by boronic esters: (a) Sadhu, K. M.; Maltesen, D. S. Organometalics 1985, 4, 1687. (b) Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795. (c) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150. (d) Brown, H. C.; Phadke, A. S.; Rangaishenvi, M. V. J. Am. Chem. Soc. 1988, 110, 6263. (e) Michnik, T. J.; Matteson, D. S. Synlett 1991, 631. (f) Wallace, R., II; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941.
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