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Volumn 131, Issue 33, 2009, Pages 11707-11711

Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION REACTION; AMINO ALCOHOLS; ANIONIC SPECIES; C-C BONDS; ELECTRON-DEFICIENT; EN-ROUTE; FUNCTIONALIZATIONS; IN-SITU; NITRENES; REDUCTION SEQUENCE;

EID: 69049104182     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9054959     Document Type: Article
Times cited : (201)

References (47)
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    • For some recent examples of asymmetric conjugate addition reactions with nitrogen nucleophiles to furnish β-amino ketones see: (a) Myers, J. K, Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959
    • For some recent examples of asymmetric conjugate addition reactions with nitrogen nucleophiles to furnish β-amino ketones see: (a) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959.
  • 14
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    • A sulfamate product analogous to 4 was generated via a chemoselective Rh-nitrene-based reaction in 43% yield: (c) Zalatan, D. N.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 9220.
    • A sulfamate product analogous to 4 was generated via a chemoselective Rh-nitrene-based reaction in 43% yield: (c) Zalatan, D. N.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 9220.
  • 17
    • 38349004623 scopus 로고    scopus 로고
    • Interestingly, high chemoselectivities and reactivities have been reported for intermolecular Rh-nitrene allylic aminations of internal olefins: Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343.
    • Interestingly, high chemoselectivities and reactivities have been reported for intermolecular Rh-nitrene allylic aminations of internal olefins: Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343.
  • 18
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    • Linear allylic C-H acetoxylation: (a) Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346.
    • Linear allylic C-H acetoxylation: (a) Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346.
  • 19
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    • Branched allylic C-H esterification: (b) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
    • Branched allylic C-H esterification: (b) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
  • 20
    • 33746094649 scopus 로고    scopus 로고
    • Oxidative C-H macrolactonization. (c) Fraunhoffer, K. J.; Prabagaran, N.; Sirois, L. E.; White, M. C. J. Am. Chem. Soc. 2006, 128, 9032.
    • Oxidative C-H macrolactonization. (c) Fraunhoffer, K. J.; Prabagaran, N.; Sirois, L. E.; White, M. C. J. Am. Chem. Soc. 2006, 128, 9032.
  • 22
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    • Linear allylic C-H alkylation: (a) Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090.
    • Linear allylic C-H alkylation: (a) Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090.
  • 23
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    • For a system that also uses Pd(II)/bis-sulfoxide catalysis see: Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901.
    • (b) For a system that also uses Pd(II)/bis-sulfoxide catalysis see: Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901.
  • 24
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    • Intramolecular allylic C-H amination to furnish 1,2-amino alcohol motifs: Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274.
    • Intramolecular allylic C-H amination to furnish 1,2-amino alcohol motifs: Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274.
  • 25
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    • Intermolecular allylic C-H amination to furnish linear (E)-allylic amines using N-(methoxycarbonyl)-p-toluenesulfonamide nucleophile: (a) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
    • Intermolecular allylic C-H amination to furnish linear (E)-allylic amines using N-(methoxycarbonyl)-p-toluenesulfonamide nucleophile: (a) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
  • 27
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    • In press, doi: /10.1021/ja903939k. For a similar system using DMA solvent see: (c) Liu, G.; Yin, G.; Wu, L. Angew. Chem., Int. Ed. 2008, 47, 4733.
    • In press, doi: /10.1021/ja903939k. For a similar system using DMA solvent see: (c) Liu, G.; Yin, G.; Wu, L. Angew. Chem., Int. Ed. 2008, 47, 4733.
  • 30
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    • Carbamate and N-tosyl carbamate substrates have been observed to exclusively form 5-membered ring oxazolidinone products in nitrene-based systems: (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
    • Carbamate and N-tosyl carbamate substrates have been observed to exclusively form 5-membered ring oxazolidinone products in nitrene-based systems: (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
  • 32
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    • The inclusion of catalytic amine base, recently discovered to promote intermolecular allylic C-H aminations with N-tosyl carbamate nucleophiles (ref 8b), gave a minor increase in yield for substrate 2a (15% → 37%); however, the diastereoselectivity was significantly diminished (5.1:1 → 1.8:1 syn:anti).
    • The inclusion of catalytic amine base, recently discovered to promote intermolecular allylic C-H aminations with N-tosyl carbamate nucleophiles (ref 8b), gave a minor increase in yield for substrate 2a (15% → 37%); however, the diastereoselectivity was significantly diminished (5.1:1 → 1.8:1 syn:anti).
  • 33
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    • This effect has explicitly been demonstrated in the oxidative amination of olefins via electrophilic Pd(II) catalysis: (a) Hegedus, L. S, McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444
    • This effect has explicitly been demonstrated in the oxidative amination of olefins via electrophilic Pd(II) catalysis: (a) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444.
  • 35
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    • Pd(0)-mediated allylic substitution of cyclic carbonates to carbamates proceeds via anionic nitrogen nucleophiles: Bando, T.; Harayama, H.; Fukazawa, Y.; Shiro, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1994, 59, 1465.
    • Pd(0)-mediated allylic substitution of cyclic carbonates to carbamates proceeds via anionic nitrogen nucleophiles: Bando, T.; Harayama, H.; Fukazawa, Y.; Shiro, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1994, 59, 1465.
  • 36
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    • Relative pKa values were based upon benzoic acid analogues: (a) Tao, L.; Han, J.; Tao, F-.M. J. Phys. Chem. A 2008, 112, 775.
    • Relative pKa values were based upon benzoic acid analogues: (a) Tao, L.; Han, J.; Tao, F-.M. J. Phys. Chem. A 2008, 112, 775.
  • 38
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    • Heating the reaction with N-tosyl carbamate substrates to 65°C also promoted reactivity; however, the yields were lower, and inconsistent results were observed.
    • Heating the reaction with N-tosyl carbamate substrates to 65°C also promoted reactivity; however, the yields were lower, and inconsistent results were observed.
  • 40
    • 33845217953 scopus 로고    scopus 로고
    • Carboxylic acids have been shown to increase reactivity in oxidative Heck reactions mediated by Pd(II)/bis-sulfoxide, possibly via acid-promoted quinone reoxidation of the metal: (b) Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076.
    • Carboxylic acids have been shown to increase reactivity in oxidative Heck reactions mediated by Pd(II)/bis-sulfoxide, possibly via acid-promoted quinone reoxidation of the metal: (b) Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076.
  • 46
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    • For previous asymmetric syntheses see: a
    • For previous asymmetric syntheses see: (a) Takahata, H.; Kubota, M.; Ikota, N. J. Org. Chem. 1999, 64, 8594.
    • (1999) J. Org. Chem , vol.64 , pp. 8594
    • Takahata, H.1    Kubota, M.2    Ikota, N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.