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Volumn 9, Issue 23, 2007, Pages 4881-4884

Rhodium-catalyzed reactions of dithiols and 1,4-bis(bromomethyl)benzenes leading to enantioenriched dithiaparacyclophanes

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EID: 36348964883     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702242x     Document Type: Article
Times cited : (50)

References (45)
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    • Vögtle, F, Ed, Wiley: Chichester
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    • For a review of the cyclophane synthesis, see
    • For a review of the cyclophane synthesis, see: Kane, V. V.; De Wolff, W. H.; Bickelhaupt, F. Tetrahedron 1994, 50, 4574.
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    • For syntheses of cyclophanes via transition-metal-catalyzed or mediated macrocyclization, see: Cobalt-catalyzed [2 + 2 + 2] cycloaddition: (a) Boñaga, L. V. R.; Zhang, H.-C.; Moretto, A. F.; Ye, H.; Gautheir, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473.
    • For syntheses of cyclophanes via transition-metal-catalyzed or mediated macrocyclization, see: Cobalt-catalyzed [2 + 2 + 2] cycloaddition: (a) Boñaga, L. V. R.; Zhang, H.-C.; Moretto, A. F.; Ye, H.; Gautheir, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473.
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    • 3-catalyzed [2 + 2 + 2] cycloaddition: (e) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784.
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    • Palladium-catalyzed coupling of enynes: (f) Weibel, D.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1217.
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    • Cycloaddition of Fischer chromium carbenes with alkynes: (h) Wang, H.; Wulff, D. W.; Rheingold, L. A. J. Am. Chem. Soc. 2003, 125, 8980.
    • Cycloaddition of Fischer chromium carbenes with alkynes: (h) Wang, H.; Wulff, D. W.; Rheingold, L. A. J. Am. Chem. Soc. 2003, 125, 8980.
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    • Intramolecular addition of rhodium carbenes: (k) Doyle, M. P.; Hu, W. Synlett 2001, 1364.
    • Intramolecular addition of rhodium carbenes: (k) Doyle, M. P.; Hu, W. Synlett 2001, 1364.
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    • Heck reaction: (m) Dyker, G.; Kadzimirsz, D.; Henkel, G. Tetrahedron Lett. 2003, 44, 7905.
    • Heck reaction: (m) Dyker, G.; Kadzimirsz, D.; Henkel, G. Tetrahedron Lett. 2003, 44, 7905.
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    • See also ref 3e
    • (e) See also ref 3e.
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    • For synthesis of dithiaparacyclophanes by transacetalization, see: a
    • For synthesis of dithiaparacyclophanes by transacetalization, see: (a) Ellis-Holder, K. K.; Peppers, B. P.; Kovalevsky, A. Y.; Diver, S. T. Org. Lett. 2006, 8, 2511.
    • (2006) Org. Lett , vol.8 , pp. 2511
    • Ellis-Holder, K.K.1    Peppers, B.P.2    Kovalevsky, A.Y.3    Diver, S.T.4
  • 38
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    • For rhodium-catalyzed reductive coupling of disulfides with alkyl halides using hydrogen as a reducing agent, see: (b) Ajiki, K, Hirano, M, Tanaka, K. Org. Lett. 2005, 7, 4193
    • For rhodium-catalyzed reductive coupling of disulfides with alkyl halides using hydrogen as a reducing agent, see: (b) Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193.
  • 39
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    • For pioneering work on a metal-catalyzed coupling reaction of thiols and alkyl iodides using a platinum complex as a catalyst, see: (a) Page, P. C. B, Klair, S. S, Brown, M. P, Harding, M. M, Smith, C. S, Maginn, S. J, Mulley, S. Tetrahedron Lett. 1988, 29, 4477
    • For pioneering work on a metal-catalyzed coupling reaction of thiols and alkyl iodides using a platinum complex as a catalyst, see: (a) Page, P. C. B.; Klair, S. S.; Brown, M. P.; Harding, M. M.; Smith, C. S.; Maginn, S. J.; Mulley, S. Tetrahedron Lett. 1988, 29, 4477.
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    • Increasing the reaction temperature decreased the yields of dithiaparacyclophanes
    • Increasing the reaction temperature decreased the yields of dithiaparacyclophanes.
  • 42
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    • Synthesis and chiroptical properties of planar-chiral dithia[n]cyclophanes were reported. For dithia[n]paracyclophanes. see ref 3e. For dithia[n]metacyclophanes, see ref 8a
    • Synthesis and chiroptical properties of planar-chiral dithia[n]cyclophanes were reported. For dithia[n]paracyclophanes. see ref 3e. For dithia[n]metacyclophanes, see ref 8a.
  • 43
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    • MOP: 2-(diphenylphosphino)-2′-methoxy-1,1′-binaphthyl. Chiraphos: 2,3-bis(diphenylphosphino)butane. DIOP: 4,5- bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane. i-Pr-Duphos: 1,2-bis(2,5-di-i-propylphospholano)benzene.
    • MOP: 2-(diphenylphosphino)-2′-methoxy-1,1′-binaphthyl. Chiraphos: 2,3-bis(diphenylphosphino)butane. DIOP: 4,5- bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane. i-Pr-Duphos: 1,2-bis(2,5-di-i-propylphospholano)benzene.
  • 44
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    • In the reactions of dithiols and dibromides shown in Tables 1 and 2 and Schemes 1 and 2, the starting materials were not recovered and insoluble oligomers were obtained as byproducts
    • In the reactions of dithiols and dibromides shown in Tables 1 and 2 and Schemes 1 and 2, the starting materials were not recovered and insoluble oligomers were obtained as byproducts.
  • 45
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    • For synthesis of fluorenedithia[3.3]paracyclophane copolymers, see: Wang, W.; Xu, J.; Lai, Y.-H. Org. Lett. 2003, 5, 2765.
    • For synthesis of fluorenedithia[3.3]paracyclophane copolymers, see: Wang, W.; Xu, J.; Lai, Y.-H. Org. Lett. 2003, 5, 2765.


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