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Volumn 73, Issue 3, 2008, Pages 1004-1007

Intermolecular hydroaminations via strained (E)-cycloalkenes

Author keywords

[No Author keywords available]

Indexed keywords

AZOLES; CYCLIC ALKENES; INTERMOLECULAR HYDROAMINATIONS;

EID: 38849104955     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701985w     Document Type: Article
Times cited : (31)

References (45)
  • 1
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    • For selected reviews, see: a
    • For selected reviews, see: (a) Matsunaga, S. J. Synth. Org. Chem. Jpn. 2006, 64, 778.
    • (2006) J. Synth. Org. Chem. Jpn , vol.64 , pp. 778
    • Matsunaga, S.1
  • 10
    • 0013168349 scopus 로고    scopus 로고
    • For a review on base-catalyzed hydroaminations, see: b
    • For a review on base-catalyzed hydroaminations, see: (b) Seayad, J.; Tillack, A.; Hartung, C. G.; Beller, M. Adv. Synth. Catal. 2002, 344, 795-813.
    • (2002) Adv. Synth. Catal , vol.344 , pp. 795-813
    • Seayad, J.1    Tillack, A.2    Hartung, C.G.3    Beller, M.4
  • 12
    • 0000410805 scopus 로고
    • For a review of the Ritter reaction, see: b
    • For a review of the Ritter reaction, see: (b) Krimen, L. I.; Cota, D. J. Org. React. 1969, 17, 213.
    • (1969) Org. React , vol.17 , pp. 213
    • Krimen, L.I.1    Cota, D.J.2
  • 17
    • 0034210728 scopus 로고    scopus 로고
    • and references cited therein
    • (c) Ostrovskii, V. A.; Koren, A. O. Heterocycles 2000, 53, 1421 (and references cited therein).
    • (2000) Heterocycles , vol.53 , pp. 1421
    • Ostrovskii, V.A.1    Koren, A.O.2
  • 19
    • 38849123962 scopus 로고    scopus 로고
    • Kelly US Patent 4,954,655, filed 03/1989
    • (a) Kelly US Patent 4,954,655, filed 03/1989.
  • 20
    • 38849179170 scopus 로고    scopus 로고
    • Eichinger; Fiege US Patent 5,585,521, filed 09/1995.
    • (b) Eichinger; Fiege US Patent 5,585,521, filed 09/1995.
  • 37
    • 0000619796 scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Marshall, J. A. Science 1970, 170, 137.
    • (1970) Science , vol.170 , pp. 137
    • Marshall, J.A.1
  • 39
    • 38849130379 scopus 로고    scopus 로고
    • In some cases, trace amounts of acid (not sufficient to promote hydroetherification) were found to be beneficial. See ref 9d
    • In some cases, trace amounts of acid (not sufficient to promote hydroetherification) were found to be beneficial. See ref 9d.
  • 43
    • 38849172263 scopus 로고    scopus 로고
    • This selectivity for the cyclic alkene in limonene, as well as the lack of reactivity observed with 1-methylcyclopentene, cyclooctene, and in control experiments performed with other cyclic alkenes (α-pinene and 2-carene, for example) strongly suggest the intermediacy of highly strained (E)-cycloalkene intermediates. We also prefer this rationale over other possibilities, including reactivity arising from azole excited states being more acidic, for example
    • This selectivity for the cyclic alkene in limonene, as well as the lack of reactivity observed with 1-methylcyclopentene, cyclooctene, and in control experiments performed with other cyclic alkenes (α-pinene and 2-carene, for example) strongly suggest the intermediacy of highly strained (E)-cycloalkene intermediates. We also prefer this rationale over other possibilities, including reactivity arising from azole excited states being more acidic, for example.
  • 44
    • 38849178495 scopus 로고    scopus 로고
    • In agreement with this rationale, the limonene recovered from the reaction shown in eq 8 was found to be racemic. See the experimental details
    • In agreement with this rationale, the limonene recovered from the reaction shown in eq 8 was found to be racemic. See the experimental details.
  • 45
    • 0000335861 scopus 로고    scopus 로고
    • See ref 12 for a discussion. For an example of application in total synthesis, see: Marshall, J. A.; Pike, M. T. J. Org. Chem. 1968, 33, 435.
    • See ref 12 for a discussion. For an example of application in total synthesis, see: Marshall, J. A.; Pike, M. T. J. Org. Chem. 1968, 33, 435.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.