메뉴 건너뛰기




Volumn 70, Issue 8, 2005, Pages 3198-3204

Metal-mediated entry to functionalized 3-substituted 3-hydroxyindolin-2- ones via regiocontrolled carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions of isatins in aqueous media

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVES; ALKYLATION; INDIUM; KETONES; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); TIN; ZINC;

EID: 17444387079     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050130w     Document Type: Article
Times cited : (76)

References (63)
  • 15
    • 0041878778 scopus 로고    scopus 로고
    • For recent reviews of allylmetal additions, see: (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763. (b) Roush, W. R.; Chemler, C. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (d) Thomas, E. J. Chem. Commun. 1997, 411. (e) Marshall, J. A. Chem. Rev. 1996, 96, 31. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
    • (2003) Chem. Rev. , vol.103 , pp. 2763
    • Denmark, S.E.1    Fu, J.2
  • 16
    • 0003913629 scopus 로고    scopus 로고
    • Otera, J., Ed.; Wiley-VCH: Weinheim, Chapter 11
    • For recent reviews of allylmetal additions, see: (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763. (b) Roush, W. R.; Chemler, C. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (d) Thomas, E. J. Chem. Commun. 1997, 411. (e) Marshall, J. A. Chem. Rev. 1996, 96, 31. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
    • (2000) Modern Carbonyl Chemistry
    • Roush, W.R.1    Chemler, C.R.2
  • 17
    • 0000554723 scopus 로고    scopus 로고
    • Otera, J., Ed.; Wiley-VCH: Weinheim, Chapter 10
    • For recent reviews of allylmetal additions, see: (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763. (b) Roush, W. R.; Chemler, C. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (d) Thomas, E. J. Chem. Commun. 1997, 411. (e) Marshall, J. A. Chem. Rev. 1996, 96, 31. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
    • (2000) Modern Carbonyl Chemistry
    • Denmark, S.E.1    Almstead, N.G.2
  • 18
    • 0002213778 scopus 로고    scopus 로고
    • For recent reviews of allylmetal additions, see: (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763. (b) Roush, W. R.; Chemler, C. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (d) Thomas, E. J. Chem. Commun. 1997, 411. (e) Marshall, J. A. Chem. Rev. 1996, 96, 31. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
    • (1997) Chem. Commun. , pp. 411
    • Thomas, E.J.1
  • 19
    • 0002313620 scopus 로고    scopus 로고
    • For recent reviews of allylmetal additions, see: (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763. (b) Roush, W. R.; Chemler, C. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (d) Thomas, E. J. Chem. Commun. 1997, 411. (e) Marshall, J. A. Chem. Rev. 1996, 96, 31. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
    • (1996) Chem. Rev. , vol.96 , pp. 31
    • Marshall, J.A.1
  • 20
    • 4243893500 scopus 로고
    • For recent reviews of allylmetal additions, see: (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763. (b) Roush, W. R.; Chemler, C. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (d) Thomas, E. J. Chem. Commun. 1997, 411. (e) Marshall, J. A. Chem. Rev. 1996, 96, 31. (f) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
    • (1993) Chem. Rev. , vol.93 , pp. 2207
    • Yamamoto, Y.1    Asao, N.2
  • 21
    • 0034247817 scopus 로고    scopus 로고
    • For reviews, see: (a) Marshall, J. A. Chem. Rev. 2000, 100, 3163. (b) Yamamoto, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.3. (c) Panek, J. S. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 595.
    • (2000) Chem. Rev. , vol.100 , pp. 3163
    • Marshall, J.A.1
  • 22
    • 0003716367 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford, Chapter 1.3
    • For reviews, see: (a) Marshall, J. A. Chem. Rev. 2000, 100, 3163. (b) Yamamoto, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.3. (c) Panek, J. S. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 595.
    • (1991) Comprehensive Organic Synthesis , vol.2
    • Yamamoto, H.1
  • 23
    • 0001512271 scopus 로고
    • Schreiber, S. L., Ed.; Pergamon Press: Oxford
    • For reviews, see: (a) Marshall, J. A. Chem. Rev. 2000, 100, 3163. (b) Yamamoto, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.3. (c) Panek, J. S. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 595.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 595
    • Panek, J.S.1
  • 24
    • 1042275565 scopus 로고    scopus 로고
    • (a) For a review on indium- and gallium-mediated reactions, including isatins, see: Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B. S. Tetrahedron 2004, 60, 1959.
    • (2004) Tetrahedron , vol.60 , pp. 1959
    • Nair, V.1    Ros, S.2    Jayan, C.N.3    Pillai, B.S.4
  • 26
    • 17444426394 scopus 로고
    • (c) For the first investigations of the Reformatsky reaction on isatins, see: Myers, F. J.; Lindwall, H. G. J. Am. Chem. Soc. 1938, 60, 644.
    • (1938) J. Am. Chem. Soc. , vol.60 , pp. 644
    • Myers, F.J.1    Lindwall, H.G.2
  • 27
    • 17444371755 scopus 로고    scopus 로고
    • note
    • (d) 3-Alkenyl 3-hydroxyindolin-2-ones can be obtained by a Claisen rearrangement; see ref 2a.
  • 32
    • 0036703508 scopus 로고    scopus 로고
    • For recents reviews on organic reactions in aqueous media, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095. (c) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299. (d) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (e) Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1. (f) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York, 1998.
    • (2002) Chem. Rev. , vol.102 , pp. 2751
    • Lindström, U.M.1
  • 33
    • 0012536208 scopus 로고    scopus 로고
    • For recents reviews on organic reactions in aqueous media, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095. (c) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299. (d) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (e) Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1. (f) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York, 1998.
    • (2002) Chem. Eur. J. , vol.8 , pp. 4095
    • Manabe, K.1    Kobayashi, S.2
  • 34
    • 0035925228 scopus 로고    scopus 로고
    • For recents reviews on organic reactions in aqueous media, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095. (c) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299. (d) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (e) Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1. (f) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York, 1998.
    • (2001) Chem. Commun. , pp. 299
    • Ribe, S.1    Wipf, P.2
  • 35
    • 0033543497 scopus 로고    scopus 로고
    • For recents reviews on organic reactions in aqueous media, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095. (c) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299. (d) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (e) Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1. (f) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York, 1998.
    • (1999) Tetrahedron , vol.55 , pp. 11149
    • Li, C.J.1    Chan, T.H.2
  • 36
    • 0002430323 scopus 로고    scopus 로고
    • For recents reviews on organic reactions in aqueous media, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095. (c) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299. (d) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (e) Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1. (f) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York, 1998.
    • (1999) Top. Curr. Chem. , vol.206 , pp. 1
    • Lubineau, A.1    Augé, J.2
  • 37
    • 0003768632 scopus 로고    scopus 로고
    • Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York
    • For recents reviews on organic reactions in aqueous media, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095. (c) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299. (d) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (e) Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1. (f) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York, 1998.
    • (1998) Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing
    • Paquette, L.A.1
  • 38
    • 0842307395 scopus 로고    scopus 로고
    • See, for instance: (a) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2004, 69, 826. (c) Alcaide, B.; Almendros, P.; Alonso, J. M. Chem. Eur. J. 2003, 9, 5793. (d) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2003, 5, 3795. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem. Eur. J. 2003, 9, 3415.
    • (2004) J. Org. Chem. , vol.69 , pp. 993
    • Alcaide, B.1    Almendros, P.2    Alonso, J.M.3
  • 39
    • 0842328942 scopus 로고    scopus 로고
    • See, for instance: (a) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2004, 69, 826. (c) Alcaide, B.; Almendros, P.; Alonso, J. M. Chem. Eur. J. 2003, 9, 5793. (d) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2003, 5, 3795. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem. Eur. J. 2003, 9, 3415.
    • (2004) J. Org. Chem. , vol.69 , pp. 826
    • Alcaide, B.1    Almendros, P.2    Aragoncillo, C.3    Rodríguez-Acebes, R.4
  • 40
    • 0347624092 scopus 로고    scopus 로고
    • See, for instance: (a) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2004, 69, 826. (c) Alcaide, B.; Almendros, P.; Alonso, J. M. Chem. Eur. J. 2003, 9, 5793. (d) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2003, 5, 3795. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem. Eur. J. 2003, 9, 3415.
    • (2003) Chem. Eur. J. , vol.9 , pp. 5793
    • Alcaide, B.1    Almendros, P.2    Alonso, J.M.3
  • 41
    • 0242628828 scopus 로고    scopus 로고
    • See, for instance: (a) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2004, 69, 826. (c) Alcaide, B.; Almendros, P.; Alonso, J. M. Chem. Eur. J. 2003, 9, 5793. (d) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2003, 5, 3795. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem. Eur. J. 2003, 9, 3415.
    • (2003) Org. Lett. , vol.5 , pp. 3795
    • Alcaide, B.1    Almendros, P.2    Aragoncillo, C.3
  • 42
    • 0041345738 scopus 로고    scopus 로고
    • See, for instance: (a) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2004, 69, 826. (c) Alcaide, B.; Almendros, P.; Alonso, J. M. Chem. Eur. J. 2003, 9, 5793. (d) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2003, 5, 3795. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem. Eur. J. 2003, 9, 3415.
    • (2003) Chem. Eur. J. , vol.9 , pp. 3415
    • Alcaide, B.1    Almendros, P.2    Alonso, J.M.3    Aly, M.F.4
  • 47
    • 5644229532 scopus 로고    scopus 로고
    • See, for example: (a) Trost, B. M.; Corte, J. R.; Gudiksen, M. S. Angew. Chem., Int. Ed. 1999, 38, 3662. (b) Crimmins, M. T.; She, J. J. Am. Chem. Soc. 2004, 126, 12790.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12790
    • Crimmins, M.T.1    She, J.2
  • 59
    • 17444413903 scopus 로고    scopus 로고
    • note
    • A reviewer pointed out the unstability of the bis organometallic intermediate on the two adjacent carbons.
  • 60
    • 0034644018 scopus 로고    scopus 로고
    • 4-Cl plays is perhaps 2-fold: (1) to activate the carbonyl group and (2) to polish the metal surface. See: (b) Zhang, J.; Blazecka, P. G.; Berven, H.; Belmont, D. Tetrahedron Lett. 2003, 44, 5579.
    • (2000) Org. Lett , vol.2 , pp. 2003
    • Chappell, M.D.1    Halcomb, R.L.2
  • 63
    • 17444413835 scopus 로고    scopus 로고
    • note
    • Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.