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Volumn 74, Issue 10, 2009, Pages 3680-3688

The scope and limitations of intramolecular Nicholas and Pauson-Khand reactions for the synthesis of tricyclic oxygen-and nitrogen-containing heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC INDUCTION; CHEMICAL EQUATIONS; CHIRAL AMINES; CYCLIC ETHER; DIOLIDES; EFFICIENT SYNTHESIS; HETEROCYCLES; NICHOLAS REACTIONS; NITROGEN-CONTAINING HETEROCYCLES; OXIDATION OF ALCOHOLS; PAUSON-KHAND; PAUSON-KHAND REACTIONS; RING SYSTEMS; STARTING MATERIALS;

EID: 65949123562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8027592     Document Type: Article
Times cited : (29)

References (50)
  • 2
    • 33845425987 scopus 로고    scopus 로고
    • For a review of tandem Nicholas/Pauson-Khand reactions see
    • For a review of tandem Nicholas/Pauson-Khand reactions see: Pérez-Castells, J. Top. Organomet. Chem. 2006, 19, 207-257.
    • (2006) Top. Organomet. Chem. , vol.19 , pp. 207-257
    • Pérez-Castells, J.1
  • 5
    • 12344266742 scopus 로고    scopus 로고
    • For preliminary reports from our lab, see:
    • For preliminary reports from our lab, see: (a) Quintal, M. M.; Closser, K. D.; Shea, K. M. Org. Lett. 2004, 6, 4949-4952.
    • (2004) Org. Lett. , vol.6 , pp. 4949-4952
    • Quintal, M.M.1    Closser, K.D.2    Shea, K.M.3
  • 7
    • 65949106117 scopus 로고    scopus 로고
    • For reviews, see: (a) Li, J. J., Ed.; Wiley: Hoboken, NJ
    • For reviews, see: (a) Shea, K. M. In Name Reactions for Homologations-1; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009; pp 284-298.
    • (2009) Name Reactions for Homologations-1 , pp. 284-298
    • Shea, K.M.1
  • 14
    • 65949101845 scopus 로고    scopus 로고
    • For a communication from our lab containing several examples of endocyclic intramolecular Nicholas reactions with alcohol nucleophiles, see ref 4a.
    • For a communication from our lab containing several examples of endocyclic intramolecular Nicholas reactions with alcohol nucleophiles, see ref 4a.
  • 15
    • 48849110611 scopus 로고    scopus 로고
    • For examples of intermolecular and exocyclic intramolecular Nicholas reactions with amine nucleophiles, see: (a)
    • For examples of intermolecular and exocyclic intramolecular Nicholas reactions with amine nucleophiles, see: (a) Hernández, J. N.; Ramìrez, M. A.; Rodrìguez, M. L.; Martìn, V. S. Org. Lett. 2008, 10, 2349-2352.
    • (2008) Org. Lett. , vol.10 , pp. 2349-2352
    • Hernández, J.N.1    Ramìrez, M.A.2    Rodrìguez, M.L.3    Martìn, V.S.4
  • 19
    • 65949096290 scopus 로고    scopus 로고
    • For a preliminary report from our lab detailing inter- and intramolecular Nicholas reactions with carboxylic acid nucleophiles, see ref 4b.
    • For a preliminary report from our lab detailing inter- and intramolecular Nicholas reactions with carboxylic acid nucleophiles, see ref 4b.
  • 23
    • 0034912138 scopus 로고    scopus 로고
    • For a review of cyclic cobalt-complexed alkynes, see
    • For a review of cyclic cobalt-complexed alkynes, see: Green, J. R. Curr. Org. Chem. 2001, 5, 809-826.
    • (2001) Curr. Org. Chem. , vol.5 , pp. 809-826
    • Green, J.R.1
  • 28
    • 65949117206 scopus 로고    scopus 로고
    • 1H NMR. Major and minor isomers were assigned by using COSY and difference NOE NMR experiments.
    • 1H NMR. Major and minor isomers were assigned by using COSY and difference NOE NMR experiments.
  • 29
    • 65949119108 scopus 로고    scopus 로고
    • Results for all of the Pauson-Khand conditions are available in ref 4a.
    • Results for all of the Pauson-Khand conditions are available in ref 4a.
  • 31
    • 0037031622 scopus 로고    scopus 로고
    • This is a known compound, see
    • This is a known compound, see: Marino, J. P.; Nguyen, H. N. J. Org. Chem. 2002, 67, 6291-6296.
    • (2002) J. Org. Chem. , vol.67 , pp. 6291-6296
    • Marino, J.P.1    Nguyen, H.N.2
  • 40
    • 65949084683 scopus 로고    scopus 로고
    • The structure of cobalt-alkyne complex 55 was not unambiguously assigned by NMR spectroscopy because the material was used immediately in the subsequent Nicholas reaction. Due to the similarity in TLC behavior to all of the other cobalt-alkyne complexes prepared in our lab, we are confident that 55 was successfully synthesized.
    • The structure of cobalt-alkyne complex 55 was not unambiguously assigned by NMR spectroscopy because the material was used immediately in the subsequent Nicholas reaction. Due to the similarity in TLC behavior to all of the other cobalt-alkyne complexes prepared in our lab, we are confident that 55 was successfully synthesized.
  • 41
    • 65949109465 scopus 로고    scopus 로고
    • 1H NMR features (very broad peaks) in comparison to diolides 59 and 62.
    • 1H NMR features (very broad peaks) in comparison to diolides 59 and 62.
  • 42
    • 65949097231 scopus 로고    scopus 로고
    • The structure of the trans isomer of 59 was confirmed by X-ray single crystal analysis; see ref 4b.
    • The structure of the trans isomer of 59 was confirmed by X-ray single crystal analysis; see ref 4b.
  • 47
    • 18044388948 scopus 로고    scopus 로고
    • For procedures that minimize or eliminate diolide formation, see:
    • For procedures that minimize or eliminate diolide formation, see: (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 2397-2400.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 2397-2400
    • Kinoshita, H.1    Shinokubo, H.2    Oshima, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.