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Volumn 70, Issue 18, 2005, Pages 7159-7171

Rh(I)-catalyzed Pauson-Khand reaction and cycloisomerization of allenynes: Selective preparation of monocyclic, bicyclo[m.3.0], and bicyclo[5.2.0] ring systems

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; DERIVATIVES; ISOMERIZATION; NITROGEN; ORGANIC COMPOUNDS; RHODIUM;

EID: 24144488325     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050770z     Document Type: Article
Times cited : (69)

References (68)
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    • (d) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037-1064
    • Schore, N.E.1
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    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York
    • (e) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, pp 703-739.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 703-739
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    • Beller, H., Bolm, C., Eds; Wiley-VCH: Weinheim
    • (g) Jeong, N. In Transition Metals in Organic Synthesis; Beller, H., Bolm, C., Eds; Wiley-VCH: Weinheim, 1998; Vol. 1, pp 560-577.
    • (1998) Transition Metals in Organic Synthesis , vol.1 , pp. 560-577
    • Jeong, N.1
  • 12
    • 0025313296 scopus 로고
    • For attempts at constructing the bicyclo[5.3.0]decenone skeleton via the intramolecular PKR of enynes, see: (a) Wender, P. A.; McDonald, F. E. Tetrahedron Lett. 1990, 31, 3691-3694.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3691-3694
    • Wender, P.A.1    McDonald, F.E.2
  • 23
    • 0001457964 scopus 로고
    • For other examples of the formation of the bicyclo[5.3.0]decane skeleton via transition metal-catalyzed PKR of allenynes, see: (a) Shibata, T.; Koga, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 911-919.
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 911-919
    • Shibata, T.1    Koga, Y.2    Narasaka, K.3
  • 30
    • 0001171594 scopus 로고    scopus 로고
    • 2 was first used in PKR by Jenog and co-workers, see: (a) Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642-3644.
    • (1998) Organometallics , vol.17 , pp. 3642-3644
    • Jeong, N.1    Lee, S.2    Sung, B.K.3
  • 32
    • 0002524474 scopus 로고
    • For reviews on cycloisomerization of enynes, see: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 34-42
    • Trost, B.M.1
  • 34
  • 35
    • 0042848783 scopus 로고    scopus 로고
    • For Rh(I)-catalyzed allenene cycloisomerization, see: (a) Makino, T.; Itoh, K. Tetrahedron Lett. 2003, 44, 6335-6338.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6335-6338
    • Makino, T.1    Itoh, K.2
  • 44
    • 33645598781 scopus 로고    scopus 로고
    • note
    • 2 could be observed.
  • 45
    • 33645585743 scopus 로고    scopus 로고
    • note
    • 2.
  • 46
    • 33645600136 scopus 로고    scopus 로고
    • note
    • 2 under 20 atm of CO, 6e was obtained in 81% yield along with 7e in 15% yield.
  • 50
    • 33645599305 scopus 로고    scopus 로고
    • note
    • (E)-Stereochemistry of 15 was determined on the basis of NOE experiments. For instance, 3.4% enhancement of vinyl protons and 1.5% enhancement of methyl group were recorded when Ha of 15c was irradiated.
  • 55
    • 33645596745 scopus 로고    scopus 로고
    • note
    • 2 could be used for transformation of 5a-c into 7a-c in slightly lower yield [7a (69%), 7b (66%), and 7c (44%)].
  • 56
    • 33645589655 scopus 로고    scopus 로고
    • note
    • Compounds 7d (6%), 7e (31%), and 7f (48%) were obtained with recovery of the starting materials 5d (72%), 5e (51%), and 5f (36%), respectively.
  • 57
    • 33645583002 scopus 로고    scopus 로고
    • note
    • 2 was found not to be a suitable catalyst for transformation of 10 into 12 [12a (30%), 12b (13%), and 12c (16%)].
  • 58
    • 33645589130 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra with those of carbon congeners.
  • 59
    • 33645584694 scopus 로고    scopus 로고
    • note
    • For example, an NOE experiment of 35b showed 6.1% enhancement of methyl group upon irradiation of vinyl proton, while 5.6% enhancement between methyl group and vinyl proton of 35c was observed.
  • 60
    • 33645593846 scopus 로고    scopus 로고
    • note
    • Data for crystallographic analysis of 35c was described in the Supporting Information.
  • 64
    • 33645584058 scopus 로고    scopus 로고
    • note
    • 1H NMR.
  • 65
    • 33645585474 scopus 로고    scopus 로고
    • note
    • Compounds 15c (10%) and 35c (42%) were isolated after refluxing a solution of 15c in xylene for 9 h.
  • 66
    • 33645588325 scopus 로고    scopus 로고
    • note
    • Compounds 36 were prepared by the standard procedure described in this paper; see the Supporting Information.
  • 67
    • 33645589395 scopus 로고    scopus 로고
    • note
    • Compounds 12d,e were exposed to xylene refluxing conditions leading to an intractable mixture.
  • 68
    • 33645593307 scopus 로고    scopus 로고
    • note
    • b bond could not be detected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.