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Volumn 61, Issue 22, 1996, Pages 7951-7954

Direct synthesis of [α-[(tert-Butoxycarbonyl)amino]alkyl]-boronates from (α-haloalkyl)boronates

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EID: 0043012078     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961075h     Document Type: Article
Times cited : (13)

References (32)
  • 19
    • 3342923002 scopus 로고    scopus 로고
    • note
    • 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.
  • 20
    • 3342973412 scopus 로고    scopus 로고
    • note
    • 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.
  • 21
    • 0001175929 scopus 로고
    • 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.
    • (1985) Organometalics , vol.4 , pp. 1687
    • Sadhu, K.M.1    Maltesen, D.S.2
  • 22
    • 0001207083 scopus 로고
    • 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.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 795
    • Sadhu, K.M.1    Matteson, D.S.2
  • 23
    • 0000253386 scopus 로고
    • 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.
    • (1986) J. Org. Chem. , vol.51 , pp. 3150
    • Brown, H.C.1    Singh, S.M.2    Rangaishenvi, M.V.3
  • 24
    • 0000871060 scopus 로고
    • 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.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6263
    • Brown, H.C.1    Phadke, A.S.2    Rangaishenvi, M.V.3
  • 25
    • 85093511443 scopus 로고
    • 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.
    • (1991) Synlett , pp. 631
    • Michnik, T.J.1    Matteson, D.S.2
  • 26
    • 0026439939 scopus 로고
    • 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.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6941
    • Wallace II, R.1    Zong, K.K.2


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