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Volumn 27, Issue 22, 2008, Pages 5984-5996

Enantioselective addition of terminal alkynes to aromatic aldehydes catalyzed by copper(I) complexes with wide-bite-angle chiral bisphosphine ligands: Optimization, scope, and mechanistic studies

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALDEHYDES; AROMATIC COMPOUNDS; COPPER; COPPER COMPOUNDS; ENANTIOSELECTIVITY; HYDROCARBONS; LIGANDS; ORGANIC COMPOUNDS; OXYGEN; PHOSPHORUS COMPOUNDS; PORT TERMINALS;

EID: 57049170859     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800667c     Document Type: Article
Times cited : (45)

References (44)
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    • For the synthesis, see: (a) Kuwano, R.; Sawamura, M. In Catalysts for Fine Chemical Synthesis, 5: Regio- and Stereo-Controlled Oxidations and Reductions; Roberts, S. M., Whittall, J., Eds.; John Wiley & Sons: West Sussex, 2007; pp 73-86.
    • For the synthesis, see: (a) Kuwano, R.; Sawamura, M. In Catalysts for Fine Chemical Synthesis, Volume 5: Regio- and Stereo-Controlled Oxidations and Reductions; Roberts, S. M., Whittall, J., Eds.; John Wiley & Sons: West Sussex, 2007; pp 73-86.
  • 14
    • 33745579608 scopus 로고    scopus 로고
    • For selected papers for the application of TRAP ligands, see: a
    • For selected papers for the application of TRAP ligands, see: (a) Kuwano, R.; Kashiwabara, M. Org. Lett. 2006, 8, 2653.
    • (2006) Org. Lett , vol.8 , pp. 2653
    • Kuwano, R.1    Kashiwabara, M.2
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    • Part of this work has been published as a communication. See
    • Part of this work has been published as a communication. See Asano, Y.; Hara, K.; Ito, H.; Sawamura, M. Org. Lett. 2007, 9, 3901.
    • (2007) Org. Lett , vol.9 , pp. 3901
    • Asano, Y.1    Hara, K.2    Ito, H.3    Sawamura, M.4
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    • For a closely related work, see
    • For a closely related work, see: Motoki, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2007, 9, 2997.
    • (2007) Org. Lett , vol.9 , pp. 2997
    • Motoki, R.1    Kanai, M.2    Shibasaki, M.3
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    • Ito, H.; Watanabe, A.; Sawamura, M. Org. Lett. 2005, 7, 1869 See also (Au catalysis):
    • (a) Ito, H.; Watanabe, A.; Sawamura, M. Org. Lett. 2005, 7, 1869 See also (Au catalysis):
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    • Ito, H.; Kawakami, C.; Sawamura, M. J. Am. Chem. Soc. 2005, 127, 16034. See also:
    • (a) Ito, H.; Kawakami, C.; Sawamura, M. J. Am. Chem. Soc. 2005, 127, 16034. See also:
  • 30
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    • For the synthesis and use of DTBM-Xantphos, see ref 15a
    • For the synthesis and use of DTBM-Xantphos, see ref 15a.
  • 31
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    • Procedures for the synthesis of DTBM-TRAP and Terph-TRAP are described in the Experimental Section
    • Procedures for the synthesis of DTBM-TRAP and Terph-TRAP are described in the Experimental Section.
  • 32
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    • For the catalysis of K(O-t-Bu) toward the addition of terminal alkynes to ketones, see: Babler, J. H.; Liptak, V. P.; Phan, N. J. Org. Chem. 1996, 61, 416.
    • For the catalysis of K(O-t-Bu) toward the addition of terminal alkynes to ketones, see: Babler, J. H.; Liptak, V. P.; Phan, N. J. Org. Chem. 1996, 61, 416.
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    • In contrast, when the same set of NMR measurements were conducted with Xantphos ligand, the signal for a complex that appeared after the addition of la was broad, and the significant signal for uncoordinated Xantphos remained. When i-Pr-DUPHOS was used as a ligand, two broad peaks were observed in the low magnetic field (see Supporting Information for NMR spectra).
    • In contrast, when the same set of NMR measurements were conducted with Xantphos ligand, the signal for a complex that appeared after the addition of la was broad, and the significant signal for uncoordinated Xantphos remained. When i-Pr-DUPHOS was used as a ligand, two broad peaks were observed in the low magnetic field (see Supporting Information for NMR spectra).
  • 38
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    • A reviewer pointed out the ambiguity of the assignment of this signal
    • A reviewer pointed out the ambiguity of the assignment of this signal.
  • 39
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    • A reviewer suggested a possibility of [2, 2] cycloaddition
    • A reviewer suggested a possibility of [2 + 2] cycloaddition.
  • 40
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    • Tsuda, T.; Hashimoto, T.; Saegusa, T. J. Am. Chem. Soc. 1972, 94, 658. See also:
    • (a) Tsuda, T.; Hashimoto, T.; Saegusa, T. J. Am. Chem. Soc. 1972, 94, 658. See also:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.