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Volumn 48, Issue 43, 2009, Pages 8066-8069

Catalytic enantioselective synthesis of chiral tetraphenylenes: Consecutive inter- and intramolecular cycloadditions of two triynes

Author keywords

Alkynes; Asymmetric synthesis; Chirality; Cycloaddition; Rhodium

Indexed keywords

ALKYNES; ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE REACTIONS; ENANTIOSELECTIVE SYNTHESIS; INTRAMOLECULAR CYCLOADDITIONS;

EID: 70349970188     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903715     Document Type: Article
Times cited : (67)

References (28)
  • 2
    • 0005056181 scopus 로고
    • For the structure determination by X-ray crystallographic study, see
    • For the structure determination by X-ray crystallographic study, see: b) H. Irngartinger, W. R. K. Reibel, Acta Crystallogr. Sect. B 1981, 37, 1724.
    • (1981) Acta Crystallogr. Sect. B , vol.37 , pp. 1724
    • Irngartinger, H.1    Reibel, W.R.K.2
  • 6
    • 0141710179 scopus 로고    scopus 로고
    • (Eds.: D. D. MacNicol, F. Toda, P. Bishop), Pergamon, Oxford
    • b) T. C. W. Mak, H. N. C. Wong in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: D. D. MacNicol, F. Toda, P. Bishop), Pergamon, Oxford, 1996, p. 351.
    • (1996) Comprehensive Supramolecular Chemistry , vol.6 , pp. 351
    • Mak, T.C.W.1    Wong, H.N.C.2
  • 22
    • 84948372490 scopus 로고
    • Co-catalyzed [2+2+2] cycloaddition of phenylene-bridged 1, 5-diynes with alkynes is an established protocol for the synthesis of substituted biphenylenes
    • Co-catalyzed [2+2+2] cycloaddition of phenylene-bridged 1, 5-diynes with alkynes is an established protocol for the synthesis of substituted biphenylenes: K. P. C. Vollhardt, Pure Appl. Chem. 1993, 65, 153.
    • (1993) Pure Appl. Chem. , vol.65 , pp. 153
    • Vollhardt, K.P.C.1
  • 23
    • 34548173261 scopus 로고    scopus 로고
    • Tanaka comprehensively studied cationic Rh-binap derivative catalyzed alkyne trimerization, see
    • Tanaka comprehensively studied cationic Rh-binap derivative catalyzed alkyne trimerization, see: K. Tanaka, Synlett 2007, 1977.
    • (2007) Synlett , pp. 1977
    • Tanaka, K.1
  • 24
    • 70349958137 scopus 로고    scopus 로고
    • The reaction of biphenylene 2ab using Rh-biphep catalyst did not give tetraphenylene 3ab at all. This result clearly denies the homo-coupling mechanism of biphenylene for the present transformation.
    • The reaction of biphenylene 2ab using Rh-biphep catalyst did not give tetraphenylene 3ab at all. This result clearly denies the homo-coupling mechanism of biphenylene for the present transformation.
  • 27
    • 70349964397 scopus 로고    scopus 로고
    • The reaction conditions were investigated on a 0.05 mmol scale, but the reaction using Rh-QuinoxP* catalyst certainly proceeded with the almost same yield and ee value (68%, 88% ee) on a 0.5 mmol scale.
    • The reaction conditions were investigated on a 0.05 mmol scale, but the reaction using Rh-QuinoxP* catalyst certainly proceeded with the almost same yield and ee value (68%, 88% ee) on a 0.5 mmol scale.
  • 28
    • 70349952139 scopus 로고    scopus 로고
    • The absolute configuration of product 3ab was determined by the circular dichroism exciton chirality method (see the Supporting Information), but the final determination was deferred to a future publication.
    • The absolute configuration of product 3ab was determined by the circular dichroism exciton chirality method (see the Supporting Information), but the final determination was deferred to a future publication.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.