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Volumn 73, Issue 7, 2008, Pages 2649-2655

A theoretical study on the trans-addition intramolecular hydroacylation of 4-alkynals catalyzed by cationic rhodium complexes

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYSIS; CYCLIZATION; METAL COMPLEXES; ORGANIC SOLVENTS; REACTION KINETICS;

EID: 41649106319     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702582j     Document Type: Article
Times cited : (25)

References (67)
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    • See for example a
    • See for example (a) Schore, N. E. Chem. Rev. 1988, 88, 1081.
    • (1988) Chem. Rev , vol.88 , pp. 1081
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    • and references therein
    • (c) Bosnich, B. Acc. Chem. Res. 1998, 31, 667 and references therein.
    • (1998) Acc. Chem. Res , vol.31 , pp. 667
    • Bosnich, B.1
  • 14
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    • Intermolecular hydroacylation of alkynes and aldehydes: (a) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564.
    • Intermolecular hydroacylation of alkynes and aldehydes: (a) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564.
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    • For recent reviews, see: d
    • For recent reviews, see: (d) Iida, H.; Krische, M. J. Top. Curr. Chem. 2007, 279, 77.
    • (2007) Top. Curr. Chem , vol.279 , pp. 77
    • Iida, H.1    Krische, M.J.2
  • 29
    • 9244234942 scopus 로고    scopus 로고
    • The intramolecular hydroacylation was also extended to 5- and 6-alkynals: Takeishi, K.; Sugishima, K.; Sasaki, K.; Tanaka, K. Chem. Eur. J. 2004, 10, 5681.
    • The intramolecular hydroacylation was also extended to 5- and 6-alkynals: Takeishi, K.; Sugishima, K.; Sasaki, K.; Tanaka, K. Chem. Eur. J. 2004, 10, 5681.
  • 30
    • 0037163266 scopus 로고    scopus 로고
    • The intramolecular hydroacylation of alkynals catalyzed by Wilkinson's catalyst to produce syn-addition of 7-m-r and 8-m-r exo-cyclization products by means of a chelating sulfur tether atom have been reported: Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031.
    • The intramolecular hydroacylation of alkynals catalyzed by Wilkinson's catalyst to produce syn-addition of 7-m-r and 8-m-r exo-cyclization products by means of a chelating sulfur tether atom have been reported: Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031.
  • 38
    • 41649113222 scopus 로고    scopus 로고
    • In most experimentally studied systems, the C5 position is substituted by an alkyl group. Preliminary calculations at the B3LYP level of theory show that the substituent effect of these groups is negligible.
    • In most experimentally studied systems, the C5 position is substituted by an alkyl group. Preliminary calculations at the B3LYP level of theory show that the substituent effect of these groups is negligible.
  • 42
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    • trans-Hydroarylation of alkynes by arenes: (a) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
    • trans-Hydroarylation of alkynes by arenes: (a) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
  • 45
    • 0141757441 scopus 로고    scopus 로고
    • trans-Hydrosilylation reaction: (a) Chung, L. W.; Wu, Y.-D.; Trost, B. M.; Zachary, B. J. Am. Chem. Soc. 2003, 125, 11578.
    • trans-Hydrosilylation reaction: (a) Chung, L. W.; Wu, Y.-D.; Trost, B. M.; Zachary, B. J. Am. Chem. Soc. 2003, 125, 11578.
  • 49
    • 0001298427 scopus 로고    scopus 로고
    • The proposed trans-addition process is originated from syn-addition, followed by isomerization and reductive elimination: (a) Tanke, R.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 7984.
    • The proposed trans-addition process is originated from syn-addition, followed by isomerization and reductive elimination: (a) Tanke, R.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 7984.
  • 51
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    • Gaussian 98, Revision A.7; M. J. Frisch, Gaussian, Inc.: Pittsburgh PA, 1998.
    • (a) Gaussian 98, Revision A.7; M. J. Frisch, Gaussian, Inc.: Pittsburgh PA, 1998.
  • 52
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    • Gaussian 03, Revision B.05; M. J. Frisch, Gaussian, Inc.: Pittsburgh PA, 2003.
    • (b) Gaussian 03, Revision B.05; M. J. Frisch, Gaussian, Inc.: Pittsburgh PA, 2003.
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    • 11-CP could not be located. The basis set superposition error introduced by this approach is expected to be small compared to the energy differences discussed here.
    • 11-CP could not be located. The basis set superposition error introduced by this approach is expected to be small compared to the energy differences discussed here.
  • 61
    • 41649113221 scopus 로고    scopus 로고
    • 11-CP (c.f. ref 20a).
    • 11-CP (c.f. ref 20a).
  • 62
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    • It should be mentioned that there is a second conformation of 2 with the hydride in the apical position that is essentially isoenergetic for the small model system discussed here. However, this conformation will be destabilized for more highly substituted systems as a result of steric repulsion and is therefore not considered further
    • It should be mentioned that there is a second conformation of 2 with the hydride in the apical position that is essentially isoenergetic for the small model system discussed here. However, this conformation will be destabilized for more highly substituted systems as a result of steric repulsion and is therefore not considered further.
  • 63
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    • Recent examples: (a) Dorta, R.; Stevens, E. D.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5054.
    • Recent examples: (a) Dorta, R.; Stevens, E. D.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5054.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.