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Volumn , Issue 19, 2009, Pages 3065-3081

Camphor derivatives in asymmetric cycloadditions and rearrangements

Author keywords

Chiral auxiliaries; Cycloadditions; Diels Alder reactions; Rearrangements, asymmetric catalysis

Indexed keywords

2 AZADIENE DERIVATIVE; AVERMECTIN; CAMPHOR DERIVATIVE; DIENOPHILE DERIVATIVE; DIPOLAROPHILE DERIVATIVE; HYDRAZINE DERIVATIVE; NATURAL PRODUCT; OXAHYDRINDANE; OXAZOLINE DERIVATIVE; OXIDE; SULFONYLHYDRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 72049100092     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218302     Document Type: Review
Times cited : (19)

References (70)
  • 1
    • 33751532023 scopus 로고
    • For a convenient, inexpensive preparation of (-)-camphor from (-)-borneol, see
    • For a convenient, inexpensive preparation of (-)-camphor from (-)-borneol, see: Stevens, R. V.; Chapman, K. T.; Weller, H. N. J. Org. Chem. 1980, 45, 2030.
    • (1980) J. Org. Chem. , vol.45 , pp. 2030
    • Stevens, R.V.1    Chapman, K.T.2    Weller, H.N.3
  • 2
    • 0038736789 scopus 로고
    • For the use of camphor derivatives in asymmetric synthesis, see: (a)
    • For the use of camphor derivatives in asymmetric synthesis, see: (a) Oppolzer, W. Tetrahedron 1987, 43, 1969.
    • (1987) Tetrahedron , vol.43 , pp. 1969
    • Oppolzer, W.1
  • 4
    • 38349178582 scopus 로고    scopus 로고
    • For a review concerning iminium catalysis, see
    • For a review concerning iminium catalysis, see: Erkkila, A.; Majander, I.; Pikho, P. M. Chem. Rev. 2007, 107, 5416.
    • (2007) Chem. Rev. , vol.107 , pp. 5416
    • Erkkila, A.1    Majander, I.2    Pikho, P.M.3
  • 6
    • 61949362917 scopus 로고    scopus 로고
    • For a recent review on enantioselective Diels-Alder reactions, see: and references cited therein.
    • For a recent review on enantioselective Diels-Alder reactions, see: Corey, E. J. Angew. Chem. Int. Ed. 2009, 48, 2100; and references cited therein.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2100
    • Corey, E.J.1
  • 8
    • 72049123561 scopus 로고    scopus 로고
    • Trifluoromethanesulfonic anhydride, even freshly distilled, promoted at -78°C the polymerization of cyclopentadiene; however, the use of methyloxirane as proton scavenger precluded this polymerization. See ref. 14.
    • Trifluoromethanesulfonic anhydride, even freshly distilled, promoted at -78°C the polymerization of cyclopentadiene; however, the use of methyloxirane as proton scavenger precluded this polymerization. See ref. 14.
  • 10
    • 72049103489 scopus 로고    scopus 로고
    • Danishefsky's diene was not stable in the presence of trifluoroacetic anhydride.
    • Danishefsky's diene was not stable in the presence of trifluoroacetic anhydride.
  • 12
    • 72049113974 scopus 로고    scopus 로고
    • All product diastereomer analyses were carried out by capillary chromatography coupled with mass spectrometric analysis or by HPLC. The four diastereomers corresponding to the adduct 21 were prepared as a sample for comparison.
    • All product diastereomer analyses were carried out by capillary chromatography coupled with mass spectrometric analysis or by HPLC. The four diastereomers corresponding to the adduct 21 were prepared as a sample for comparison.
  • 14
    • 72049110023 scopus 로고    scopus 로고
    • For a recent review concerning the preparation of amino alcohol 36, see: (a) See also
    • For a recent review concerning the preparation of amino alcohol 36, see: (a) White, J. D.; Wardrop, D. J.; Sundermann, K. F. Org. Synth. 2002, 79. See also:
    • (2002) Org. Synth. , pp. 79
    • White, J.D.1    Wardrop, D.J.2    Sundermann, K.F.3
  • 17
    • 72049087293 scopus 로고    scopus 로고
    • 2O.
    • 2O.
  • 19
    • 72049123826 scopus 로고    scopus 로고
    • Cycloadduct 54 was prepared independently by thiophenylation of adduct 26 of known configuration. The configurations at C2 in adducts 55, 56, and 57 were deduced after NMR experiments.
    • Cycloadduct 54 was prepared independently by thiophenylation of adduct 26 of known configuration. The configurations at C2 in adducts 55, 56, and 57 were deduced after NMR experiments.
  • 21
    • 84952078360 scopus 로고
    • For a review concerning avermectin synthesis, see
    • For a review concerning avermectin synthesis, see: Blizzard, T. A. Org. Prep. Proced. Int. 1994, 26, 617.
    • (1994) Org. Prep. Proced. Int. , vol.26 , pp. 617
    • Blizzard, T.A.1
  • 27
    • 34547400063 scopus 로고    scopus 로고
    • For [3+2] cycloadditions of camphor-derived nitrones, see: (a)
    • For [3+2] cycloadditions of camphor-derived nitrones, see: (a) Ali, S. A.; Iman, N. Z. N. Tetrahedron 2007, 63, 9134.
    • (2007) Tetrahedron , vol.63 , pp. 9134
    • Ali, S.A.1    Iman, N.Z.N.2
  • 30
    • 72049118530 scopus 로고    scopus 로고
    • Unpublished results from our laboratory.
    • Unpublished results from our laboratory.
  • 43
    • 67249121541 scopus 로고    scopus 로고
    • For a synthesis of tetrahydrolipstatin, see: and references cited therein
    • For a synthesis of tetrahydrolipstatin, see: Ghosh, A. K.; Shurrush, K.; Kulkarni, S. J. Org. Chem. 2009, 74, 4508; and references cited therein.
    • (2009) J. Org. Chem. , vol.74 , pp. 4508
    • Ghosh, A.K.1    Shurrush, K.2    Kulkarni, S.3
  • 45
  • 49
    • 0001688963 scopus 로고
    • For a recent review, see
    • (a) Blaise, E. E. C. R. Acad. Sci. 1901, 132, 478. For a recent review, see::
    • (1901) Acad. Sci. , vol.132 , pp. 478
    • Blaise, E.E.C.R.1
  • 53
    • 7544241609 scopus 로고    scopus 로고
    • For syntheses of carbocyclic nucleosides, see: and references cited therein
    • For syntheses of carbocyclic nucleosides, see: Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235; and references cited therein.
    • (2004) Antiviral Chem. Chemother. , vol.15 , pp. 235
    • Jeong, L.S.1    Lee, J.A.2
  • 56
    • 84988066006 scopus 로고
    • For a review on radical denitration, see
    • For a review on radical denitration, see: Ono, N.; Kaji, A. Synthesis 1986, 693.
    • (1986) Synthesis , pp. 693
    • Ono, N.1    Kaji, A.2
  • 64
    • 53249140774 scopus 로고    scopus 로고
    • For organocatalyzed Diels-Alder cycloadditions, see: and references cited therein
    • For organocatalyzed Diels-Alder cycloadditions, see: Hayashi, Y.; Samanta, S.; Gotoh, H.; Ishikawa, H. Angew. Chem. Int. Ed. 2008, 47, 6634; and references cited therein.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6634
    • Hayashi, Y.1    Samanta, S.2    Gotoh, H.3    Ishikawa, H.4
  • 65
    • 34547224498 scopus 로고    scopus 로고
    • During the completion of this work, the use of camphoric acid hydrazides as catalysts in Diels-Alder cycloaddition was reported; see: and references cited therein
    • During the completion of this work, the use of camphoric acid hydrazides as catalysts in Diels-Alder cycloaddition was reported; see: Lemay, M.; Aumand, L.; Ogilvie, W. W. Adv. Synth. Catal. 2007, 349, 441; and references cited therein.
    • (2007) Adv. Synth. Catal. , vol.349 , pp. 441
    • Lemay, M.1    Aumand, L.2    Ogilvie, W.W.3
  • 66
    • 48849100725 scopus 로고    scopus 로고
    • Almost the same study was reported before the publication of our own work
    • Almost the same study was reported before the publication of our own work: He, H.; Pei, B.-J.; Chou, H.-H.; Tian, T.; Lee, A. W. M. Org. Lett. 2008, 10, 2421.
    • (2008) Org. Lett. , vol.10 , pp. 2421
    • He, H.1    Pei, B.-J.2    Chou, H.-H.3    Tian, T.4    Lee, A.W.M.5
  • 68
    • 67650079016 scopus 로고    scopus 로고
    • For a recent use of camphor-derived sulfonylhydrazines in an aza-Michael addition, see
    • For a recent use of camphor-derived sulfonylhydrazines in an aza-Michael addition, see: Chen, L.-Y.; He, H.; Pei, B.-J.; Chan, W.-H.; Lee, A. W. M. Synthesis 2009, 1573.
    • (2009) Synthesis , pp. 1573
    • Chen, L.-Y.1    He, H.2    Pei, B.-J.3    Chan, W.-H.4    Lee, A.W.M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.