메뉴 건너뛰기




Volumn 41, Issue 24, 2002, Pages 4693-4697

An efficient one-pot enantio- and diastereoselective synthesis of heterocycles

Author keywords

Alkylation; Asymmetric synthesis; Heterocycles; Homogeneous catalysis; Palladium; Ruthenium

Indexed keywords

ALKYLATION; CATALYSTS; NITROGEN; OXYGEN; SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 0037122149     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290019     Document Type: Article
Times cited : (53)

References (37)
  • 1
    • 0001146788 scopus 로고    scopus 로고
    • P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206; See also: H. Hopf, J. Wolff, Eur. J. Org. Chem. 2001, 4009-4030; B. M. Trost, A. J. Frontier, J. Am. Chem. Soc. 2000, 122, 11727-11728; K. Neuschuetz, J. Velker, R. Neier, Synthesis 1998, 227-255; J. Markandu, H. A. Dondas, M. Frederickson, R. Grigg, Tetrahedron 1997, 53, 13165-13176.
    • (1996) Chem. Rev. , vol.96 , pp. 195-206
    • Parsons, P.J.1    Penkett, C.S.2    Shell, A.J.3
  • 2
    • 0035153894 scopus 로고    scopus 로고
    • P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206; See also: H. Hopf, J. Wolff, Eur. J. Org. Chem. 2001, 4009-4030; B. M. Trost, A. J. Frontier, J. Am. Chem. Soc. 2000, 122, 11727-11728; K. Neuschuetz, J. Velker, R. Neier, Synthesis 1998, 227-255; J. Markandu, H. A. Dondas, M. Frederickson, R. Grigg, Tetrahedron 1997, 53, 13165-13176.
    • (2001) Eur. J. Org. Chem. , pp. 4009-4030
    • Hopf, H.1    Wolff, J.2
  • 3
    • 0034730992 scopus 로고    scopus 로고
    • P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206; See also: H. Hopf, J. Wolff, Eur. J. Org. Chem. 2001, 4009-4030; B. M. Trost, A. J. Frontier, J. Am. Chem. Soc. 2000, 122, 11727-11728; K. Neuschuetz, J. Velker, R. Neier, Synthesis 1998, 227-255; J. Markandu, H. A. Dondas, M. Frederickson, R. Grigg, Tetrahedron 1997, 53, 13165-13176.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11727-11728
    • Trost, B.M.1    Frontier, A.J.2
  • 4
    • 0031931419 scopus 로고    scopus 로고
    • P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206; See also: H. Hopf, J. Wolff, Eur. J. Org. Chem. 2001, 4009-4030; B. M. Trost, A. J. Frontier, J. Am. Chem. Soc. 2000, 122, 11727-11728; K. Neuschuetz, J. Velker, R. Neier, Synthesis 1998, 227-255; J. Markandu, H. A. Dondas, M. Frederickson, R. Grigg, Tetrahedron 1997, 53, 13165-13176.
    • (1998) Synthesis , pp. 227-255
    • Neuschuetz, K.1    Velker, J.2    Neier, R.3
  • 5
    • 0343307026 scopus 로고    scopus 로고
    • P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206; See also: H. Hopf, J. Wolff, Eur. J. Org. Chem. 2001, 4009-4030; B. M. Trost, A. J. Frontier, J. Am. Chem. Soc. 2000, 122, 11727-11728; K. Neuschuetz, J. Velker, R. Neier, Synthesis 1998, 227-255; J. Markandu, H. A. Dondas, M. Frederickson, R. Grigg, Tetrahedron 1997, 53, 13165-13176.
    • (1997) Tetrahedron , vol.53 , pp. 13165-13176
    • Markandu, J.1    Dondas, H.A.2    Frederickson, M.3    Grigg, R.4
  • 7
    • 0036371962 scopus 로고    scopus 로고
    • B. M. Trost, Chem. Pharm. Bull. 2002, 50, 1-14; B. M. Trost, C. Lee, Catalytic Asymmetric Synthesis 11, (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 593-650; B. M. Trost, D. C. Van Vranken, Chem. Rev. 1995, 95, 395-422.
    • (2002) Chem. Pharm. Bull. , vol.50 , pp. 1-14
    • Trost, B.M.1
  • 8
    • 0036371962 scopus 로고    scopus 로고
    • (Ed.: I. Ojima), Wiley-VCH, New York
    • B. M. Trost, Chem. Pharm. Bull. 2002, 50, 1-14; B. M. Trost, C. Lee, Catalytic Asymmetric Synthesis 11, (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 593-650; B. M. Trost, D. C. Van Vranken, Chem. Rev. 1995, 95, 395-422.
    • (2000) Catalytic Asymmetric Synthesis 11 , pp. 593-650
    • Trost, B.M.1    Lee, C.2
  • 9
    • 0036371962 scopus 로고    scopus 로고
    • B. M. Trost, Chem. Pharm. Bull. 2002, 50, 1-14; B. M. Trost, C. Lee, Catalytic Asymmetric Synthesis 11, (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 593-650; B. M. Trost, D. C. Van Vranken, Chem. Rev. 1995, 95, 395-422.
    • (1995) Chem. Rev. , vol.95 , pp. 395-422
    • Trost, B.M.1    Van Vranken, D.C.2
  • 11
    • 0035385137 scopus 로고    scopus 로고
    • in press
    • B. M. Trost, Acc. Chem. Res. 2002, 35, in press; B. M. Trost, F. D. Toste, A. B. Pinkerton, Chem. Rev. 2001, 101, 2067-2096.
    • (2002) Acc. Chem. Res. , pp. 35
    • Trost, B.M.1
  • 13
    • 0001580179 scopus 로고    scopus 로고
    • T. P. Gill, K. R. Mann, Organometallics 1982, 1, 485-488. For an improved procedure, see: B. M. Trost, C. M. Older, Organometallics 2002, 8, 2455-2546.
    • (1982) Organometallics , vol.1 , pp. 485-488
    • Gill, T.P.1    Mann, K.R.2
  • 14
    • 0001580179 scopus 로고    scopus 로고
    • T. P. Gill, K. R. Mann, Organometallics 1982, 1, 485-488. For an improved procedure, see: B. M. Trost, C. M. Older, Organometallics 2002, 8, 2455-2546.
    • (2002) Organometallics , vol.8 , pp. 2455-2546
    • Trost, B.M.1    Older, C.M.2
  • 17
    • 0034684229 scopus 로고    scopus 로고
    • Other dual transition metal sequences: N. Jeong, S. Deok, J. Y. Shin, J. Am. Chem. Soc. 2000, 122, 10220-10221; T. Doi, M. Kobuko, K. Yamamoto, T. Takahashi, Org. Syn. 1998, 6, 428-429; a recent example of catalytic sequences with Ru-catalyzed ene-yne coupling: F. Lopez, L. Castedo, J. L. Mascarenas, J. Am. Chem. Soc. 2002, 124, 4218-4219.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 10220-10221
    • Jeong, N.1    Deok, S.2    Shin, J.Y.3
  • 18
    • 0037165687 scopus 로고    scopus 로고
    • Other dual transition metal sequences: N. Jeong, S. Deok, J. Y. Shin, J. Am. Chem. Soc. 2000, 122, 10220-10221; T. Doi, M. Kobuko, K. Yamamoto, T. Takahashi, Org. Syn. 1998, 6, 428-429; a recent example of catalytic sequences with Ru-catalyzed ene-yne coupling: F. Lopez, L. Castedo, J. L. Mascarenas, J. Am. Chem. Soc. 2002, 124, 4218-4219.
    • (1998) Org. Syn. , vol.6 , pp. 428-429
    • Doi, T.1    Kobuko, M.2    Yamamoto, K.3    Takahashi, T.4
  • 19
    • 0037165687 scopus 로고    scopus 로고
    • Other dual transition metal sequences: N. Jeong, S. Deok, J. Y. Shin, J. Am. Chem. Soc. 2000, 122, 10220-10221; T. Doi, M. Kobuko, K. Yamamoto, T. Takahashi, Org. Syn. 1998, 6, 428-429; a recent example of catalytic sequences with Ru-catalyzed ene-yne coupling: F. Lopez, L. Castedo, J. L. Mascarenas, J. Am. Chem. Soc. 2002, 124, 4218-4219.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4218-4219
    • Lopez, F.1    Castedo, L.2    Mascarenas, J.L.3
  • 21
    • 0037087753 scopus 로고    scopus 로고
    • B. M. Trost, P. Fraisse, Z. T. Ball, Angew. Chem. 2002, 114, 1101-1103; Angew. Chem. Int. Ed. 2002, 41, 1059-1061.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1059-1061
  • 22
    • 0000547520 scopus 로고
    • K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1973, 46, 1012-1013; D. G. Brady, Chem. Commun. 1970, 434-435; I. Onoue Moritani, S. I. Murahashi, Tetrahedron Lett. 1977, 121-124; J. C. Fiaud, A. Hibon de Gournay, M. Larchevegere, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; J. Tsuji, Y. Kobayashi, T Takahashi, Tetrahedron Lett. 1980, 21, 3393-3394; for a review see: B. M. Trost, T. R. Verhoeven in Comprehansive Organometalic Chemistry, Vol. 8, 1st ed. (Eds.; G. Wilkinson, F. G. A. Stone, E. Abel), Pergamon, Oxford, 1982, p. 799-938.
    • (1972) Bull. Chem. Soc. Jpn. , vol.45 , pp. 230-236
    • Takahashi, K.1    Miyake, A.2    Hata, G.3
  • 23
    • 0346854817 scopus 로고
    • K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1973, 46, 1012-1013; D. G. Brady, Chem. Commun. 1970, 434-435; I. Onoue Moritani, S. I. Murahashi, Tetrahedron Lett. 1977, 121-124; J. C. Fiaud, A. Hibon de Gournay, M. Larchevegere, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; J. Tsuji, Y. Kobayashi, T Takahashi, Tetrahedron Lett. 1980, 21, 3393-3394; for a review see: B. M. Trost, T. R. Verhoeven in Comprehansive Organometalic Chemistry, Vol. 8, 1st ed. (Eds.; G. Wilkinson, F. G. A. Stone, E. Abel), Pergamon, Oxford, 1982, p. 799-938.
    • (1973) Bull. Chem. Soc. Jpn. , vol.46 , pp. 1012-1013
    • Takahashi, K.1    Miyake, A.2    Hata, G.3
  • 24
    • 37049140434 scopus 로고
    • K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1973, 46, 1012-1013; D. G. Brady, Chem. Commun. 1970, 434-435; I. Onoue Moritani, S. I. Murahashi, Tetrahedron Lett. 1977, 121-124; J. C. Fiaud, A. Hibon de Gournay, M. Larchevegere, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; J. Tsuji, Y. Kobayashi, T Takahashi, Tetrahedron Lett. 1980, 21, 3393-3394; for a review see: B. M. Trost, T. R. Verhoeven in Comprehansive Organometalic Chemistry, Vol. 8, 1st ed. (Eds.; G. Wilkinson, F. G. A. Stone, E. Abel), Pergamon, Oxford, 1982, p. 799-938.
    • (1970) Chem. Commun. , pp. 434-435
    • Brady, D.G.1
  • 25
    • 0348115493 scopus 로고
    • K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1973, 46, 1012-1013; D. G. Brady, Chem. Commun. 1970, 434-435; I. Onoue Moritani, S. I. Murahashi, Tetrahedron Lett. 1977, 121-124; J. C. Fiaud, A. Hibon de Gournay, M. Larchevegere, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; J. Tsuji, Y. Kobayashi, T Takahashi, Tetrahedron Lett. 1980, 21, 3393-3394; for a review see: B. M. Trost, T. R. Verhoeven in Comprehansive Organometalic Chemistry, Vol. 8, 1st ed. (Eds.; G. Wilkinson, F. G. A. Stone, E. Abel), Pergamon, Oxford, 1982, p. 799-938.
    • (1977) Tetrahedron Lett. , pp. 121-124
    • Onoue Moritani, I.1    Murahashi, S.I.2
  • 26
    • 0000518909 scopus 로고
    • K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1973, 46, 1012-1013; D. G. Brady, Chem. Commun. 1970, 434-435; I. Onoue Moritani, S. I. Murahashi, Tetrahedron Lett. 1977, 121-124; J. C. Fiaud, A. Hibon de Gournay, M. Larchevegere, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; J. Tsuji, Y. Kobayashi, T Takahashi, Tetrahedron Lett. 1980, 21, 3393-3394; for a review see: B. M. Trost, T. R. Verhoeven in Comprehansive Organometalic Chemistry, Vol. 8, 1st ed. (Eds.; G. Wilkinson, F. G. A. Stone, E. Abel), Pergamon, Oxford, 1982, p. 799-938.
    • (1978) J. Organomet. Chem. , vol.154 , pp. 175-185
    • Fiaud, J.C.1    Hibon de Gournay, A.2    Larchevegere, M.3    Kagan, H.B.4
  • 27
    • 0348115492 scopus 로고
    • K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1973, 46, 1012-1013; D. G. Brady, Chem. Commun. 1970, 434-435; I. Onoue Moritani, S. I. Murahashi, Tetrahedron Lett. 1977, 121-124; J. C. Fiaud, A. Hibon de Gournay, M. Larchevegere, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; J. Tsuji, Y. Kobayashi, T Takahashi, Tetrahedron Lett. 1980, 21, 3393-3394; for a review see: B. M. Trost, T. R. Verhoeven in Comprehansive Organometalic Chemistry, Vol. 8, 1st ed. (Eds.; G. Wilkinson, F. G. A. Stone, E. Abel), Pergamon, Oxford, 1982, p. 799-938.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 3393-3394
    • Tsuji, J.1    Kobayashi, Y.2    Takahashi, T.3
  • 28
    • 84942767100 scopus 로고
    • (Eds.; G. Wilkinson, F. G. A. Stone, E. Abel), Pergamon, Oxford
    • K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1973, 46, 1012-1013; D. G. Brady, Chem. Commun. 1970, 434-435; I. Onoue Moritani, S. I. Murahashi, Tetrahedron Lett. 1977, 121-124; J. C. Fiaud, A. Hibon de Gournay, M. Larchevegere, H. B. Kagan, J. Organomet. Chem. 1978, 154, 175-185; J. Tsuji, Y. Kobayashi, T Takahashi, Tetrahedron Lett. 1980, 21, 3393-3394; for a review see: B. M. Trost, T. R. Verhoeven in Comprehansive Organometalic Chemistry, Vol. 8, 1st ed. (Eds.; G. Wilkinson, F. G. A. Stone, E. Abel), Pergamon, Oxford, 1982, p. 799-938.
    • (1982) Comprehansive Organometalic Chemistry, Vol. 8, 1st Ed. , pp. 799-938
    • Trost, B.M.1    Verhoeven, T.R.2
  • 29
    • 0346854816 scopus 로고    scopus 로고
    • note
    • This compound has been fully characterized by spectroscopic methods and the elemental composition has been established by high-resolution mass spectrometry and/or combustion analysis.
  • 30
    • 0029119899 scopus 로고
    • T. Fukayama, C. K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373 -6374; T. Fukuyama, M. Cheung, C. K. Jow,; Y. Hidai, T. Kan, Tetrahedron Lett. 1997. 38, 5831-5834.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6373-6374
    • Fukayama, T.1    Jow, C.K.2    Cheung, M.3
  • 34
    • 0032481394 scopus 로고    scopus 로고
    • Simple alkyl alcohol nucleophiles can be used if the boron cocatalyst turns the intermolecular delivery into an intramolecular one: B. M. Trost, E. MacEachern, F. D. Toste, J. Am. Chem. Soc. 1998, 120, 815-816.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 815-816
    • Trost, B.M.1    MacEachern, E.2    Toste, F.D.3
  • 37
    • 0346224292 scopus 로고    scopus 로고
    • note
    • The assignment of relative configuration was straightforward by NMR spectroscopy. Since the absolute stereochemistry of the starting substrate is known, the absolute configuration of the newly created allylic stereogenic center is also known. These stereochemical assignments are furthermore consistent with our mnemonic and with those made in Table 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.