메뉴 건너뛰기




Volumn 9, Issue 7, 2007, Pages 1295-1298

Enantioselective synthesis of C2-symmetric spirobipyridine ligands through cationic Rh(I)/modified-BINAP-catalyzed double [2 + 2 + 2] cycloaddition

Author keywords

[No Author keywords available]

Indexed keywords


EID: 34147113797     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070129e     Document Type: Article
Times cited : (92)

References (71)
  • 19
    • 0346780615 scopus 로고    scopus 로고
    • For our first report on the cationic rhodium(I)/modified-BINAP-catalyzed inter- and intramolecular [2 + 2 + 2] cycloadditions, see: Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697.
    • For our first report on the cationic rhodium(I)/modified-BINAP-catalyzed inter- and intramolecular [2 + 2 + 2] cycloadditions, see: Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697.
  • 31
    • 33845252502 scopus 로고    scopus 로고
    • For recent reviews of pyridine synthesis by transition-metal-catalyzed [2 + 2 + 2] cycloadditions, see: (a) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307.
    • For recent reviews of pyridine synthesis by transition-metal-catalyzed [2 + 2 + 2] cycloadditions, see: (a) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307.
  • 34
    • 37049116387 scopus 로고    scopus 로고
    • For pioneering work on the transition-metal-catalyzed [2 + 2 + 2] cycloadditions of alkynes with nitriles, see: (a) Wakatsuki, Y.; Yamazaki, H. J. Chem. Soc., Chem. Commun. 1973, 280.
    • For pioneering work on the transition-metal-catalyzed [2 + 2 + 2] cycloadditions of alkynes with nitriles, see: (a) Wakatsuki, Y.; Yamazaki, H. J. Chem. Soc., Chem. Commun. 1973, 280.
  • 38
    • 84980156703 scopus 로고    scopus 로고
    • For pioneering work on the Co-catalyzed [2 + 2 + 2] cycloadditions of α, ω-diynes with nitriles and cyanoalkynes with monoalkynes, see: (a) Naiman, A.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1977, 16, 708.
    • For pioneering work on the Co-catalyzed [2 + 2 + 2] cycloadditions of α, ω-diynes with nitriles and cyanoalkynes with monoalkynes, see: (a) Naiman, A.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1977, 16, 708.
  • 41
    • 0034609693 scopus 로고    scopus 로고
    • Recent examples of pyridine synthesis through transition-metalcatalyzed [2 + 2 + 2] cycloadditions: Co(I): (a) Fatland, A. W.; Eaton, B. E. Org. Lett. 2000, 2, 3131.
    • Recent examples of pyridine synthesis through transition-metalcatalyzed [2 + 2 + 2] cycloadditions: Co(I): (a) Fatland, A. W.; Eaton, B. E. Org. Lett. 2000, 2, 3131.
  • 54
    • 33746299182 scopus 로고    scopus 로고
    • Yamamoto, Y.; Kinpara, K.; Ogawa, R.; Nishiyama, H.; Itoh, K. Chem.-Eur. J. 2006, 12, 5618. Ni(0):
    • (n) Yamamoto, Y.; Kinpara, K.; Ogawa, R.; Nishiyama, H.; Itoh, K. Chem.-Eur. J. 2006, 12, 5618. Ni(0):
  • 57
    • 0023363316 scopus 로고    scopus 로고
    • For pioneering work on the Rh-catalyzed [2 + 2 + 2] cycloadditions of alkynes with nitriles, see: (a) Cioni, P.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Ronca, P. J. Mol Catal. 1987, 40, 337.
    • For pioneering work on the Rh-catalyzed [2 + 2 + 2] cycloadditions of alkynes with nitriles, see: (a) Cioni, P.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Ronca, P. J. Mol Catal. 1987, 40, 337.
  • 59
    • 34147122043 scopus 로고    scopus 로고
    • For examples of pyridine synthesis through [2, 2, 2] cycloadditions using stoichiometric amounts of transition metals, see: (a) Takahashi, T, Tsai, F.-Y, Kotora, M. J. Am. Chem. Soc. 2000, 722, 4994
    • For examples of pyridine synthesis through [2 + 2 + 2] cycloadditions using stoichiometric amounts of transition metals, see: (a) Takahashi, T.; Tsai, F.-Y.; Kotora, M. J. Am. Chem. Soc. 2000, 722, 4994.
  • 63
    • 34147178367 scopus 로고    scopus 로고
    • Synthesis of bipyridines and terpyridines by transition-metal-catalyzed [2 + 2 + 2] cycloadditions: Co(I): (a) Varela, J. A.; Castedo, L; Saà, C. J. Org. Chem. 1997, 62, 4189.
    • Synthesis of bipyridines and terpyridines by transition-metal-catalyzed [2 + 2 + 2] cycloadditions: Co(I): (a) Varela, J. A.; Castedo, L; Saà, C. J. Org. Chem. 1997, 62, 4189.
  • 65
    • 0035802952 scopus 로고    scopus 로고
    • Varela, J. A.; Castedo, L.; Maestro, M.; Mania, J.; Saà, C. Chem.-Eur. J. 2001, 7, 5203. Ru(II): see refs 11k and 11n.
    • (c) Varela, J. A.; Castedo, L.; Maestro, M.; Mania, J.; Saà, C. Chem.-Eur. J. 2001, 7, 5203. Ru(II): see refs 11k and 11n.
  • 66
    • 34147130717 scopus 로고    scopus 로고
    • Recently, Yamamoto and co-workers reported that a cyanoalkyne failed to react with 1-hexyne intermolecularly in the presence of [Cp*RuClcod, catalyst, but intramolecular [2, 2, 2] cycloadditions of cyanodiynes proceeded to give tricyclic pyridines in the presence of the same Ru catalyst, although a diluted reaction condition or a slow addition is necessary. See ref 11n
    • Recently, Yamamoto and co-workers reported that a cyanoalkyne failed to react with 1-hexyne intermolecularly in the presence of [Cp*RuCl(cod)] catalyst, but intramolecular [2 + 2 + 2] cycloadditions of cyanodiynes proceeded to give tricyclic pyridines in the presence of the same Ru catalyst, although a diluted reaction condition or a slow addition is necessary. See ref 11n.
  • 69
    • 34147140843 scopus 로고    scopus 로고
    • 8-BINAP 60% ee.
    • 8-BINAP 60% ee.
  • 71
    • 34147132770 scopus 로고    scopus 로고
    • Because the first annulation and the second annulation proceed simultaneously, the monoannulation product 11 could not be isolated.
    • Because the first annulation and the second annulation proceed simultaneously, the monoannulation product 11 could not be isolated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.