Download PDF
Synthesis 2010(2): 304-314  
DOI: 10.1055/s-0029-1217126
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Ring Enlargement of Carbohydrate-Derived 1,2-Oxazines to Enantiopure 5-Bromo-1,2-oxazepines and Subsequent Palladium-Catalyzed Reactions

Ahmed Al-Harrasia,b, Sebastian Fischera, Reinhold Zimmera, Hans-Ulrich Reissig*a
a Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany
Fax: +49(30)83855367; e-Mail: hans.reissig@chemie.fu-berlin.de;
b Department of Chemistry, College of Science, Sultan Qaboos University, Alkhod 123, Sultanate of Oman
Further Information

Publication History

Received 14 August 2009
Publication Date:
20 November 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Dibromocarbene addition to d-glyceraldehyde-derived 1,2-oxazines syn -1 and anti -1 provided dibromocyclopropane intermediates syn-3 and anti-3, which smoothly reacted with methanol under ring enlargement to furnish 5-bromo-1,2-oxazepine derivatives syn -4 and anti -4. Related 1,2-oxazines such as arabinose-derived­ compounds furnished the 1,2-oxazepine derivatives syn-4e and anti-4f with fair efficacy. The alkenyl bromide moiety of 1,2-oxazepine derivatives syn -4 and anti -4 was then exploited for the introduction of new substituents via palladium-catalyzed C-C bond forming processes (Sonogashira, Suzuki, Stille, and Heck reactions). These transformations led to a series of new highly substituted 1,2-oxazepine derivatives syn-5 or anti-5-11 being of considerable interest for further synthetic elaborations.

Key words

1,2-oxazines - carbene additions - cyclopropanes - ring enlargement - 1,2-oxazepines - palladium catalysis - alkynes

    References

  • 1 For a recent review, see: Brasholz M. Reissig H.-U. Zimmer R. Acc. Chem. Res.  2009,  42:  45 
    CrossrefGoogle Scholar
  • 2a Schade W. Reissig H.-U. Synlett  1999,  632 
    Google Scholar
  • 2b Pulz R. Cicchi S. Brandi A. Reissig H.-U. Eur. J. Org. Chem.  2003,  1153 
    Google Scholar
  • 2c Helms M. Schade W. Pulz R. Watanabe T. Al-Harrasi A. Fišera L. Hlobilová I. Zahn G. Reissig H.-U. Eur. J. Org. Chem.  2005,  1003 
    Google Scholar
  • For alternative approaches to synthetically very versatile 1,2-oxazines, see:
  • 2d Zimmer R. Reissig H.-U. Angew. Chem., Int. Ed. Engl.  1988,  27:  1518 ; Angew. Chem. 1988, 100, 1576
    Google Scholar
  • 2e Hippeli C. Zimmer R. Reissig H.-U. Liebigs Ann. Chem.  1990,  469 
    Google Scholar
  • 2f Hippeli C. Reissig H.-U. Liebigs Ann. Chem.  1990,  475 
    Google Scholar
  • 2g Reissig H.-U. Hippeli C. Arnold T. Chem. Ber.  1990,  123:  2403 
    Google Scholar
  • 2h Reissig H.-U. Homann K. Hiller F. Zimmer R. Synthesis  2007,  2681 
    Google Scholar
  • 2i Zimmer R. Collas M. Czerwonka R. Hain U. Reissig H.-U. Synthesis  2008,  237 
    Google Scholar
  • 2j Zimmer R. Schmidt E. Andrä M. Duhs M.-A. Linder I. Reissig H.-U. Beilstein J. Org. Chem.  2009,  5: No. 44
    Google Scholar
  • 3a Pulz R. Watanabe T. Schade W. Reissig H.-U. Synlett  2000,  983 
    Google Scholar
  • 3b Pulz R. Al-Harrasi A. Reissig H.-U. Org. Lett.  2002,  4:  2353 
    Google Scholar
  • 3c Pulz R. Schade W. Reissig H.-U. Synlett  2003,  405 
    Google Scholar
  • 3d Al-Harrasi A. Reissig H.-U. Synlett  2005,  1152 
    Google Scholar
  • 3e Bressel B. Egart B. Al-Harrasi A. Pulz R. Reissig H.-U. Brüdgam I. Eur. J. Org. Chem.  2008,  467 
    Google Scholar
  • 4a Pulz R. Al-Harrasi A. Reissig H.-U. Synlett  2002,  817 
    Google Scholar
  • 4b Al-Harrasi A. Reissig H.-U. Angew. Chem. Int. Ed.  2005,  44:  6227 ; Angew. Chem. 2005, 117, 6383
    Google Scholar
  • 4c Pfrengle F. Al-Harrasi A. Brüdgam I. Reissig H.-U. Eur. J. Org. Chem.  2009,  282 
    Google Scholar
  • 4d Bressel B. Reissig H.-U. Org. Lett.  2009,  11:  527 
    Google Scholar
  • 4e Pfrengle F. Lentz D. Reissig H.-U. Angew. Chem. Int. Ed.  2009,  48:  3165 ; Angew. Chem. 2009, 121, 3211
    Google Scholar
  • 5a Yekta S. Prisyazhnyuk V. Reissig H.-U. Synlett  2007,  2069 
    Google Scholar
  • 5b Al-Harrasi A. Pfrengle F. Prisyazhnyuk V. Yekta S. Koóš P. Reissig H.-U. Chem. Eur. J.  2009,  15:  11632 
    Google Scholar
  • 6 For a preliminary communication, see: Al-Harrasi A. Reissig H.-U. Synlett  2005,  2376 
    Article in Thieme ConnectGoogle Scholar
  • 7a Halton B. Harvey J. Synlett  2006,  1975 
    Google Scholar
  • 7b Fedorynski M. Chem. Rev.  2003,  103:  1099 
    Google Scholar
  • 7c Léonel E. Lejaye M. Oudeyer S. Paugam JP. Nedelec J.-Y. Tetrahedron Lett.  2004,  45:  2635 
    Google Scholar
  • 7d For a review on gem-dihalocyclopropanes in organic synthesis, see: Kostikov RR. Molchanov AP. Top. Curr. Chem.  1990,  155:  41 
    Google Scholar
  • 7e Schleyer PvR. Van Dine GW. Schöllkopf U. Paust J. J. Am. Chem. Soc.  1966,  88:  2868 
    Google Scholar
  • 7f Foote CS. J. Am. Chem. Soc.  1964,  86:  1853 
    Google Scholar
  • 7g Skattebøl L. J. Org. Chem.  1966,  31:  1554 
    Google Scholar
  • 7h Skell PS. Sandler SR. J. Am. Chem. Soc.  1958,  80:  2024 
    Google Scholar
  • 8a Yale HL. Sowinski F. J. Med. Chem.  1964,  7:  609 
    Google Scholar
  • 8b Yale HL. Beer B. Pluscec J. Spitzmiller ER. J. Med. Chem.  1970,  13:  713 
    Google Scholar
  • 8c Melloni P. Della T. Arturo M. Ambrosini A. Rossi AC. J. Med. Chem.  1979,  22:  183 
    Google Scholar
  • 8d Kurihara T. Sakamoto Y. Matsumoto H. Kawabata N. Harusawa S. Yoneda R. Chem. Pharm. Bull.  1994,  42:  475 
    Google Scholar
  • 8e Levin JI. Venkatesan AM. Chan PS. Bailey TK. Vice G. Coupet J. Bioorg. Med. Chem. Lett.  1994,  4:  1819 
    Google Scholar
  • 8f Andersen KE, Olsen UB, Petersen H, Groenvald FC, Sonnewald U, Joergensen TK, and Andersen HS. inventors; Patent WO  9518793.  ; Chem. Abstr. 1995, 123, 313776
  • 8g Katano K, Satoh T, Soneda T, Kamitoh N, Fujishima K, and Hachisu M. inventors; Patent EP  878475.  ; Chem. Abstr. 1998, 130, 14000
  • 8h Hansen AJ, Jorgensen TK, and Olsen UB. inventors; Patent WO  0032193.  ; Chem. Abstr. 2000, 133, 34425
  • 8i Sakata K, Tsuji T, Tokumasu M, Takahashi K, Hirasawa S, and Ezaki J. inventors; Patent WO  02096891.  ; Chem. Abstr. 2002, 138, 14080
  • 8j Yamada Y, Takahashi K, and Hashimoto M. inventors; WO  03101489.  ; Chem. Abstr. 2003, 140, 19878
  • 9a Bremner JB. In Comprehensive Heterocyclic Chemistry II   Vol. 9:  Katritzky AR. Rees CW. Scriven EFV. Elsevier; Oxford: 1996.  p.183 
    Google Scholar
  • 9b Kratzel M. J. Chem. Soc., Perkin Trans. 1  1994,  1541 
    Google Scholar
  • 10a The conversions were performed analogously to: Raman CV. Murali R. Nagarjan M. J. Org. Chem.  1997,  62:  7694 
    Google Scholar
  • For other ring expansions of dibromocyclopropanes, see:
  • 10b Maeda H. Hirai T. Sugimoto A. Mizuno K. J. Org. Chem.  2003,  68:  7700 
    Google Scholar
  • 10c Miller TA. Bulman AL. Thompson CD. Garst ME. Macdonald TL. J. Med. Chem.  1997,  40:  3836 
    Google Scholar
  • 10d Loozen HJ. Robben WH. Richter TL. Buck HM. J. Org. Chem.  1976,  41:  384 
    Google Scholar
  • For a related ring expansion leading to septanosides, see:
  • 10e Ganesh NV. Jayaraman N. J. Org. Chem.  2009,  74:  739 
    Google Scholar
  • 11a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett.  1975,  4467 
    Google Scholar
  • 11b Sonogashira K. J. Organomet. Chem.  2002,  653:  46 
    Google Scholar
  • 11c Marsden JA. Haley MM. In Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.  p.319 
    Google Scholar
  • 11d For a scope of reaction conditions, see: Sonogashira K. In Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998.  p.203 
    Google Scholar
  • Reviews:
  • 12a Bellina F. Carpita A. Rossi R. Synthesis  2004,  2419 
    Google Scholar
  • 12b Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Google Scholar
  • 12c Miyaura N. In Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.  p.41 
    Google Scholar
  • Reviews:
  • 13a Mitchell TN. In Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.  p.125 
    Google Scholar
  • 13b Espinet P. Echavarren AM. Angew. Chem. Int. Ed.  2004,  43:  4704 ; Angew. Chem. 2004, 116, 4808
    Google Scholar
  • Reviews:
  • 14a Beletskaya IP. Cheprakov AV. Chem. Rev.  2000,  100:  3009 
    Google Scholar
  • 14b Bräse S. de Meijere A. In Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.  p.217 
    Google Scholar
  • 14c Heck RF. Nolley JP. J. Am Chem. Soc.  1968,  90:  5518 
    Google Scholar
  • 14d Heck RF. Acc. Chem. Res.  1979,  12:  146 
    Google Scholar
  • Google Scholar
  • 15a Review: Burke MD. Schreiber SL. Angew. Chem. Int. Ed.  2004,  43:  46 ; Angew. Chem. 2004, 116, 48
    Google Scholar
  • For selected original articles, see:
  • 15b Yu M. Pagenkopf PL. Org. Lett.  2003,  5:  5099 
    Google Scholar
  • 15c Young IS. Kerr MA. Org. Lett.  2004,  6:  139 
    Google Scholar
  • 15d Kim DH. Chung YK. Chem. Commun.  2005,  1634 
    Google Scholar
  • 15e Spandl RJ. Bender A. Spring DR. Org. Biomol. Chem.  2008,  6:  1149 
    Google Scholar