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Volumn 9, Issue 7, 2007, Pages 1215-1218

Direct intermolecular hydroacylation of N,N-dialkylacrylamides with aldehydes catalyzed by a cationic rhodium(I)/dppb complex

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EID: 34147095358     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070153s     Document Type: Article
Times cited : (92)

References (53)
  • 1
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    • For examples of Rh-catalyzed intramolecular hydroacylation of 4-alkenals, see: (a) Sakai, K, Ide, J, Nakamura, N. Tetrahedron Lett. 1972, 13,1287
    • For examples of Rh-catalyzed intramolecular hydroacylation of 4-alkenals, see: (a) Sakai, K.; Ide, J.; Nakamura, N. Tetrahedron Lett. 1972, 13,1287.
  • 10
    • 0035930039 scopus 로고    scopus 로고
    • For examples of Rh-catalyzed intramolecular hydroacylation of 4-alkynals, see: (a) Tanaka, K, Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492
    • For examples of Rh-catalyzed intramolecular hydroacylation of 4-alkynals, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492.
  • 13
    • 0025763126 scopus 로고
    • For synthesis of larger cyclic compounds via Rh-catalyzed intramolecular hydroacylation, see: a
    • For synthesis of larger cyclic compounds via Rh-catalyzed intramolecular hydroacylation, see: (a) Gable, K. P.; Benz, G. A. Tetrahedron Lett. 1991, 32, 3473.
    • (1991) Tetrahedron Lett , vol.32 , pp. 3473
    • Gable, K.P.1    Benz, G.A.2
  • 15
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    • Sato, Y.; Oonishi, Y.; Mori, M. Angew. Chem., Int. Ed. 2002, 41, 1218.
    • (c) Sato, Y.; Oonishi, Y.; Mori, M. Angew. Chem., Int. Ed. 2002, 41, 1218.
  • 19
    • 0008120743 scopus 로고
    • For Rh-catalyzed intermolecular hydroacylation, see: a
    • For Rh-catalyzed intermolecular hydroacylation, see: (a) Scwartz, J.; Cannon, J. B. J. Am. Chem. Soc. 1974, 96, 4721.
    • (1974) J. Am. Chem. Soc , vol.96 , pp. 4721
    • Scwartz, J.1    Cannon, J.B.2
  • 24
    • 0000643368 scopus 로고
    • For Ru-catalyzed intermolecular hydroacylation, see: a
    • For Ru-catalyzed intermolecular hydroacylation, see: (a) Kondo, T.; Tsuji, Y.; Watanabe, Y. Tetrahedron Lett. 1987, 28, 6229.
    • (1987) Tetrahedron Lett , vol.28 , pp. 6229
    • Kondo, T.1    Tsuji, Y.2    Watanabe, Y.3
  • 27
    • 33751553536 scopus 로고
    • For Ni-catalyzed intermolecular hydroacylation, see
    • For Ni-catalyzed intermolecular hydroacylation, see: Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554.
    • (1990) J. Org. Chem , vol.55 , pp. 2554
    • Tsuda, T.1    Kiyoi, T.2    Saegusa, T.3
  • 28
    • 0030996489 scopus 로고    scopus 로고
    • For Co-catalyzed intermolecular hydroacylation, see: a
    • For Co-catalyzed intermolecular hydroacylation, see: (a) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 3165
    • Lenges, C.P.1    Brookhart, M.2
  • 41
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    • Very recently, Willis et al. reported that coordination of the O atom of the hemilabile P-O-P ligand to rhodium increased the stability of the active catalyst. See
    • Very recently, Willis et al. reported that coordination of the O atom of the hemilabile P-O-P ligand to rhodium increased the stability of the active catalyst. See: Moxham, G. L.; Randell-Sly, H. E.; Brayshaw, S. K.; Woodward, R. L.; Weller, A. S.; Willis, M. C. Angew. Chem., Int. Ed. 2006, 45, 7618.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 7618
    • Moxham, G.L.1    Randell-Sly, H.E.2    Brayshaw, S.K.3    Woodward, R.L.4    Weller, A.S.5    Willis, M.C.6
  • 51
    • 34147155822 scopus 로고    scopus 로고
    • 1H NMR analysis of the crude reaction mixture.
    • 1H NMR analysis of the crude reaction mixture.
  • 52
    • 34147141903 scopus 로고    scopus 로고
    • 1H NMR analysis of the crude reaction mixture.
    • 1H NMR analysis of the crude reaction mixture.
  • 53
    • 0037059958 scopus 로고    scopus 로고
    • Treatment of aldehyde 1a or 1d and N,N- dimethylmethacrylamide (2c) with dppb (5 mol %) at 80 °C for 5 h furnished no hydroacylation product. This result denies the possibility of a dppb-catalyzed Stetter reaction. For tributylphosphine-mediated Stetter reaction of arylaldehydes and N,N-dialkylacrylamides, see: Gong, J. H.; Im, Y. J.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2002, 43, 1247.
    • Treatment of aldehyde 1a or 1d and N,N- dimethylmethacrylamide (2c) with dppb (5 mol %) at 80 °C for 5 h furnished no hydroacylation product. This result denies the possibility of a dppb-catalyzed Stetter reaction. For tributylphosphine-mediated Stetter reaction of arylaldehydes and N,N-dialkylacrylamides, see: Gong, J. H.; Im, Y. J.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2002, 43, 1247.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.