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Volumn 62, Issue 4, 1997, Pages 780-781

o-Carborane as a Novel Protective Group for Aldehydes and Ketones

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EID: 0000425082     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962130p     Document Type: Article
Times cited : (31)

References (20)
  • 2
    • 0000275815 scopus 로고
    • Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286. Evans, D. A.; Hoffman, J. M.; Truesdale, L. K. J. Am. Chem. Soc. 1973, 95, 5822. Hiyama, T.; Oishi, H.; Saimoto, H. Tetrahedron Lett. 1985, 26, 2459. Also see ref 1.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 5286
    • Stork, G.1    Maldonado, L.2
  • 3
    • 0000812802 scopus 로고
    • Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286. Evans, D. A.; Hoffman, J. M.; Truesdale, L. K. J. Am. Chem. Soc. 1973, 95, 5822. Hiyama, T.; Oishi, H.; Saimoto, H. Tetrahedron Lett. 1985, 26, 2459. Also see ref 1.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 5822
    • Evans, D.A.1    Hoffman, J.M.2    Truesdale, L.K.3
  • 4
    • 0001530076 scopus 로고
    • Also see ref 1
    • Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286. Evans, D. A.; Hoffman, J. M.; Truesdale, L. K. J. Am. Chem. Soc. 1973, 95, 5822. Hiyama, T.; Oishi, H.; Saimoto, H. Tetrahedron Lett. 1985, 26, 2459. Also see ref 1.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2459
    • Hiyama, T.1    Oishi, H.2    Saimoto, H.3
  • 5
    • 0344368655 scopus 로고
    • On the other hand, the latter property can become an advantage of the protecting group. Very high asymmetric induction is accomplished by the Lewis acid-mediated reactions of chiral acetals: Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817. Johnson, W. S.; Elliott, R.; Elliott, D. J. Am. Chem. Soc. 1983, 105, 2904. Johnson, W. S.; Edington, C.; Elliott, J. D.; Silverman, I. R. J. Am. Chem. Soc. 1984, 106, 7588. Yamamoto, Y.; Nishii, S.; Yamada, J. J. Am. Chem. Soc. 1986, 108, 7116. Also see the recent review: Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 325-354.
    • (1977) Angew. Chem., Int. Ed. Engl. , vol.16 , pp. 817
    • Mukaiyama, T.1
  • 6
    • 33845550948 scopus 로고
    • On the other hand, the latter property can become an advantage of the protecting group. Very high asymmetric induction is accomplished by the Lewis acid-mediated reactions of chiral acetals: Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817. Johnson, W. S.; Elliott, R.; Elliott, D. J. Am. Chem. Soc. 1983, 105, 2904. Johnson, W. S.; Edington, C.; Elliott, J. D.; Silverman, I. R. J. Am. Chem. Soc. 1984, 106, 7588. Yamamoto, Y.; Nishii, S.; Yamada, J. J. Am. Chem. Soc. 1986, 108, 7116. Also see the recent review: Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 325-354.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2904
    • Johnson, W.S.1    Elliott, R.2    Elliott, D.3
  • 7
    • 33845470030 scopus 로고
    • On the other hand, the latter property can become an advantage of the protecting group. Very high asymmetric induction is accomplished by the Lewis acid-mediated reactions of chiral acetals: Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817. Johnson, W. S.; Elliott, R.; Elliott, D. J. Am. Chem. Soc. 1983, 105, 2904. Johnson, W. S.; Edington, C.; Elliott, J. D.; Silverman, I. R. J. Am. Chem. Soc. 1984, 106, 7588. Yamamoto, Y.; Nishii, S.; Yamada, J. J. Am. Chem. Soc. 1986, 108, 7116. Also see the recent review: Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 325-354.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 7588
    • Johnson, W.S.1    Edington, C.2    Elliott, J.D.3    Silverman, I.R.4
  • 8
    • 33845374196 scopus 로고
    • On the other hand, the latter property can become an advantage of the protecting group. Very high asymmetric induction is accomplished by the Lewis acid-mediated reactions of chiral acetals: Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817. Johnson, W. S.; Elliott, R.; Elliott, D. J. Am. Chem. Soc. 1983, 105, 2904. Johnson, W. S.; Edington, C.; Elliott, J. D.; Silverman, I. R. J. Am. Chem. Soc. 1984, 106, 7588. Yamamoto, Y.; Nishii, S.; Yamada, J. J. Am. Chem. Soc. 1986, 108, 7116. Also see the recent review: Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 325-354.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7116
    • Yamamoto, Y.1    Nishii, S.2    Yamada, J.3
  • 9
    • 0000530344 scopus 로고
    • Pergamon Press: Oxford
    • On the other hand, the latter property can become an advantage of the protecting group. Very high asymmetric induction is accomplished by the Lewis acid-mediated reactions of chiral acetals: Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817. Johnson, W. S.; Elliott, R.; Elliott, D. J. Am. Chem. Soc. 1983, 105, 2904. Johnson, W. S.; Edington, C.; Elliott, J. D.; Silverman, I. R. J. Am. Chem. Soc. 1984, 106, 7588. Yamamoto, Y.; Nishii, S.; Yamada, J. J. Am. Chem. Soc. 1986, 108, 7116. Also see the recent review: Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 325-354.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 325-354
    • Schreiber, S.L.1
  • 10
    • 0001101889 scopus 로고
    • It was reported that generation of monolithiocarborane 2 by treating o-carborane with n-BuLi was accompanied by dilithiocarborane formation due to the disproportionate reaction of 2 (see Gome, F. A.; Johnson, S. E.; Hawthorne, M. F. J. Am. Chem. Soc. 1991, 113, 5915). However, we have found that the redistribution reaction can be avoided by carrying out the lithiation of o-carborane under controlled conditions (see a representative example in text).
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5915
    • Gome, F.A.1    Johnson, S.E.2    Hawthorne, M.F.3
  • 11
    • 1542615874 scopus 로고    scopus 로고
    • note
    • o-Carborane (closo) is converted to nido-o-carborane by treatment with bases. However, under the cleavage conditions, the closo frame-work was stable to KOH.
  • 12
    • 1542406657 scopus 로고    scopus 로고
    • note
    • Other attractive points of this protective group are that protected aldehydes and ketones 3 are readily crystallized and stable to air, moisture, and acids.
  • 13
    • 85087193857 scopus 로고    scopus 로고
    • note
    • 4 (2 equiv) for 2 days gave no benzaldehyde, but 3b was recovered quantitatively.
  • 14
    • 85087193723 scopus 로고    scopus 로고
    • note
    • 3) δ 7.87 (m, 3H), 7.78 (s, 1H), 7.54 (m, 2H), 7.45 (dd, J = 9.0, 2.0 Hz, 1H), 5.44 (d, J = 3.5 Hz, 1H), 3.84 (s, 1H), 2.72 (d, J = 3.5 Hz, 1H).
  • 18
    • 0004150764 scopus 로고
    • Academic Press: New York
    • Carboranes Grimes, R. N., Ed.; Academic Press: New York, 1970; pp 82-115.
    • (1970) Carboranes , pp. 82-115
    • Grimes, R.N.1
  • 19
    • 0009032289 scopus 로고
    • The bifunctional molecule 11 was synthesized via Heck reaction of p-bromobenzaldehyde and 5-hexen-2-one, which was prepared by the literature procedure: Buntin, S. A.; Heck, R. F. Org. Synth. 1993, 61, 82.
    • (1993) Org. Synth. , vol.61 , pp. 82
    • Buntin, S.A.1    Heck, R.F.2


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