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Volumn 125, Issue 29, 2003, Pages 8862-8869

Palladium-catalyzed asymmetric arylation, vinylation, and allenylation of tert-cyclobutanols via enantioselective C-C bond cleavage

Author keywords

[No Author keywords available]

Indexed keywords

BOND CLEAVAGE;

EID: 0038637020     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035293l     Document Type: Article
Times cited : (215)

References (115)
  • 1
    • 0009679346 scopus 로고
    • For reviews of C-C bond cleavage reactions, see: (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (d) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999; pp 97-129.
    • (1976) Chem. Rev. , vol.76 , pp. 461
    • Bishop K.C. III1
  • 2
    • 17344362973 scopus 로고
    • For reviews of C-C bond cleavage reactions, see: (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (d) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999; pp 97-129.
    • (1985) Chem. Rev. , vol.85 , pp. 245
    • Crabtree, R.H.1
  • 3
    • 0001525227 scopus 로고
    • For reviews of C-C bond cleavage reactions, see: (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (d) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999; pp 97-129.
    • (1994) Chem. Rev. , vol.94 , pp. 2241
    • Jennings, P.W.1    Johnson, L.L.2
  • 4
    • 0033119285 scopus 로고    scopus 로고
    • For reviews of C-C bond cleavage reactions, see: (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (d) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999; pp 97-129.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 870
    • Rybtchinski, B.1    Milstein, D.2
  • 5
    • 0002583629 scopus 로고    scopus 로고
    • Murai, S., Ed.; Springer: New York
    • For reviews of C-C bond cleavage reactions, see: (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (d) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999; pp 97-129.
    • (1999) Activation of Unreactive Bonds and Organic Synthesis , pp. 97-129
    • Murakami, M.1    Ito, Y.2
  • 78
    • 0001339418 scopus 로고
    • For other approaches for C-C bond cleavage, in which a direct electrophilic attack of the palladium cationic complex to an electron-rich β-carbon atom of siloxycyclopropanes occurs, see: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296. (b) Aoki, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 1541. (c) Aoki, S.; Nakamura, E. Synlett 1990, 741. (d) Fujimura, T.; Aoki, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809. (e) Aoki, S.; Nakamura, E. Tetrahedron 1991, 47, 3935. (f) Kang, S.-K.; Yamaguchi, T.; Ho, P.-S.; Kim, W.-Y.; Yoon, S.-K. Tetrahedron Lett. 1997, 38, 1947. (g) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y.; Ii, A.; Yoshida, Z.; Saidi, M. R. Tetrahedron Lett. 1992, 33, 789.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3296
    • Aoki, S.1    Fujimura, T.2    Nakamura, E.3    Kuwajima, I.4
  • 79
    • 0000387213 scopus 로고
    • For other approaches for C-C bond cleavage, in which a direct electrophilic attack of the palladium cationic complex to an electron-rich β-carbon atom of siloxycyclopropanes occurs, see: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296. (b) Aoki, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 1541. (c) Aoki, S.; Nakamura, E. Synlett 1990, 741. (d) Fujimura, T.; Aoki, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809. (e) Aoki, S.; Nakamura, E. Tetrahedron 1991, 47, 3935. (f) Kang, S.-K.; Yamaguchi, T.; Ho, P.-S.; Kim, W.-Y.; Yoon, S.-K. Tetrahedron Lett. 1997, 38, 1947. (g) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y.; Ii, A.; Yoshida, Z.; Saidi, M. R. Tetrahedron Lett. 1992, 33, 789.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 1541
    • Aoki, S.1    Nakamura, E.2    Kuwajima, I.3
  • 80
    • 0005700377 scopus 로고
    • For other approaches for C-C bond cleavage, in which a direct electrophilic attack of the palladium cationic complex to an electron-rich β-carbon atom of siloxycyclopropanes occurs, see: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296. (b) Aoki, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 1541. (c) Aoki, S.; Nakamura, E. Synlett 1990, 741. (d) Fujimura, T.; Aoki, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809. (e) Aoki, S.; Nakamura, E. Tetrahedron 1991, 47, 3935. (f) Kang, S.-K.; Yamaguchi, T.; Ho, P.-S.; Kim, W.-Y.; Yoon, S.-K. Tetrahedron Lett. 1997, 38, 1947. (g) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y.; Ii, A.; Yoshida, Z.; Saidi, M. R. Tetrahedron Lett. 1992, 33, 789.
    • (1990) Synlett , pp. 741
    • Aoki, S.1    Nakamura, E.2
  • 81
    • 0001703895 scopus 로고
    • For other approaches for C-C bond cleavage, in which a direct electrophilic attack of the palladium cationic complex to an electron-rich β-carbon atom of siloxycyclopropanes occurs, see: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296. (b) Aoki, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 1541. (c) Aoki, S.; Nakamura, E. Synlett 1990, 741. (d) Fujimura, T.; Aoki, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809. (e) Aoki, S.; Nakamura, E. Tetrahedron 1991, 47, 3935. (f) Kang, S.-K.; Yamaguchi, T.; Ho, P.-S.; Kim, W.-Y.; Yoon, S.-K. Tetrahedron Lett. 1997, 38, 1947. (g) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y.; Ii, A.; Yoshida, Z.; Saidi, M. R. Tetrahedron Lett. 1992, 33, 789.
    • (1991) J. Org. Chem. , vol.56 , pp. 2809
    • Fujimura, T.1    Aoki, S.2    Nakamura, E.3
  • 82
    • 0025824988 scopus 로고
    • For other approaches for C-C bond cleavage, in which a direct electrophilic attack of the palladium cationic complex to an electron-rich β-carbon atom of siloxycyclopropanes occurs, see: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296. (b) Aoki, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 1541. (c) Aoki, S.; Nakamura, E. Synlett 1990, 741. (d) Fujimura, T.; Aoki, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809. (e) Aoki, S.; Nakamura, E. Tetrahedron 1991, 47, 3935. (f) Kang, S.-K.; Yamaguchi, T.; Ho, P.-S.; Kim, W.-Y.; Yoon, S.-K. Tetrahedron Lett. 1997, 38, 1947. (g) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y.; Ii, A.; Yoshida, Z.; Saidi, M. R. Tetrahedron Lett. 1992, 33, 789.
    • (1991) Tetrahedron , vol.47 , pp. 3935
    • Aoki, S.1    Nakamura, E.2
  • 83
    • 0031575811 scopus 로고    scopus 로고
    • For other approaches for C-C bond cleavage, in which a direct electrophilic attack of the palladium cationic complex to an electron-rich β-carbon atom of siloxycyclopropanes occurs, see: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296. (b) Aoki, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 1541. (c) Aoki, S.; Nakamura, E. Synlett 1990, 741. (d) Fujimura, T.; Aoki, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809. (e) Aoki, S.; Nakamura, E. Tetrahedron 1991, 47, 3935. (f) Kang, S.-K.; Yamaguchi, T.; Ho, P.-S.; Kim, W.-Y.; Yoon, S.-K. Tetrahedron Lett. 1997, 38, 1947. (g) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y.; Ii, A.; Yoshida, Z.; Saidi, M. R. Tetrahedron Lett. 1992, 33, 789.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1947
    • Kang, S.-K.1    Yamaguchi, T.2    Ho, P.-S.3    Kim, W.-Y.4    Yoon, S.-K.5
  • 84
    • 0026595228 scopus 로고
    • For other approaches for C-C bond cleavage, in which a direct electrophilic attack of the palladium cationic complex to an electron-rich β-carbon atom of siloxycyclopropanes occurs, see: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296. (b) Aoki, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 1541. (c) Aoki, S.; Nakamura, E. Synlett 1990, 741. (d) Fujimura, T.; Aoki, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809. (e) Aoki, S.; Nakamura, E. Tetrahedron 1991, 47, 3935. (f) Kang, S.-K.; Yamaguchi, T.; Ho, P.-S.; Kim, W.-Y.; Yoon, S.-K. Tetrahedron Lett. 1997, 38, 1947. (g) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y.; Ii, A.; Yoshida, Z.; Saidi, M. R. Tetrahedron Lett. 1992, 33, 789.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 789
    • Yasui, K.1    Fugami, K.2    Tanaka, S.3    Tamaru, Y.4    Ii, A.5    Yoshida, Z.6    Saidi, M.R.7
  • 96
    • 0007818437 scopus 로고
    • Abstract II. Kyoto, Japan, March
    • Rhodium-catalyzed asymmetric hydrogenolysis of the α-carbon-carbon bond of cyclobutanone involving an enantioselective C-C bond cleavage was presented by: Murakami, M.; Amii, H.; Ito, Y. Abstract II. 69th Annual Meeting of the Chemical Society of Japan; Kyoto, Japan, March 1995; p 1127.
    • (1995) 69th Annual Meeting of the Chemical Society of Japan , pp. 1127
    • Murakami, M.1    Amii, H.2    Ito, Y.3
  • 98
    • 0038241989 scopus 로고    scopus 로고
    • note
    • (R)-BINAP, dppe, dppb, and dppf stand for (R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,2-bis(diphenylphosphino)ethane, 1,4-bis(diphenylphosphino)butane, and 1,1′-bis(diphenylphosphino)ferrocene, respectively. (R)-Tol-BINAP, (R)-(S)-BPPFA, (+)-Me-DUPHOS, and (+)-DIOP also stand for (R)-2,2′-bis(di-p-tolyl-diphenylphosphino)-1,1′-binaphthyl. (R)-N,N-dimethyl-1-[(S)-1′,2-bis(diphenylphosphino)ferrocenyl] ethylamine, (+)-1,2-bis(2,5-dimethylphospholano)benzene, and (+)-4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane, respectively.
  • 101
    • 0030470857 scopus 로고    scopus 로고
    • (-)-Sparteine-mediated enantioselective lithiation of N-Boc-N-(p-methoxy-phenyl)-cinnamylamine followed by treatment with benzyl bromide provided (S)-N-Boc-N-(p-methoxyphenyl)-3,4-diphenyl-(Z)-1-butene-1-amine. Subsequent hydrolysis with HCl to the corresponding aldehyde followed by Grignard reaction with PhMgBr afforded the corresponding alcohol which was then oxidized to give (S)-(-)-1a. The S-configuration of 1a obtained in this asymmetric arylation was confirmed by both the specific rotation and the retention time of HPLC. Absolute configurations of (S)-(-)-5a and (S)-(+)-1o were confirmed in the same way. (a) Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218.(b) Whisler, M. C.; Soli, E. D.; Beak, P. Tetrahedron Lett. 2000, 41, 9527.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12218
    • Weisenburger, G.A.1    Beak, P.2
  • 102
    • 0034598021 scopus 로고    scopus 로고
    • (-)-Sparteine-mediated enantioselective lithiation of N-Boc-N-(p-methoxy-phenyl)-cinnamylamine followed by treatment with benzyl bromide provided (S)-N-Boc-N-(p-methoxyphenyl)-3,4-diphenyl-(Z)-1-butene-1-amine. Subsequent hydrolysis with HCl to the corresponding aldehyde followed by Grignard reaction with PhMgBr afforded the corresponding alcohol which was then oxidized to give (S)-(-)-1a. The S-configuration of 1a obtained in this asymmetric arylation was confirmed by both the specific rotation and the retention time of HPLC. Absolute configurations of (S)-(-)-5a and (S)-(+)-1o were confirmed in the same way. (a) Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218.(b) Whisler, M. C.; Soli, E. D.; Beak, P. Tetrahedron Lett. 2000, 41, 9527.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 9527
    • Whisler, M.C.1    Soli, E.D.2    Beak, P.3
  • 105
  • 107
    • 0038580760 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of cis-9 and trans-9.
  • 109
    • 33751055792 scopus 로고
    • (a) Tsuji, J. Palladium Reagents and Catalysis; Innovations in Organic Synthesis, Wiley: Chichester, 1995. (b) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2589
    • Tsuji, J.1    Mandai, T.2
  • 113


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