PDF herunterladen
Synlett 2011(11): 1579-1584  
DOI: 10.1055/s-0030-1260775
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Dramatic Base-Oriented Chemoselective Tandem Wacker Cyclizations: Synthesis of Bisbenzannelated Spiroketals and 2-Substituted Chromans

Zhijun Xin, Yuan Zhang, Hua Tao, Jijun Xue*, Ying Li*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: xuejj@lzu.edu.cn; e-Mail: liying@lzu.edu.cn;
Weitere Informationen

Publikationsverlauf

Received 7 March 2011
Publikationsdatum:
10. Juni 2011 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A Pd(II)/Cu(II)-catalyzed chemoselective tandem aerobic cyclization of phenolic olefins leads to [5,6]-bisbenzannelated spiroketals or 2-substituted chromans, wherein it was interestingly found that the presence or absence of base could be responsible for the tunable selectivity. The [5,6]-bisbenzannelated spiroketals were achieved from tandem Wacker cyclization-aroxylation in moderate yields in the absence of base, and 2-substituted chromans were formed through base-mediated Pd(II)/Cu(II)-catalyzed tandem Wacker cyclization-Michael addition in good yields.

Key words

palladium - chemoselectivity - spiroketals - chromans - Wacker cyclization

    References

  • 1 Kuramochi A. Usuda H. Yamatsugu K. Kanai M. Shibasaki M. J. Am. Chem. Soc.  2005,  127:  14200 
    Suche in Google Scholar
  • 2 Korotchenko VN. Gagne MR. J. Org. Chem.  2007,  72:  4877 
    CrossrefSuche in Google Scholar
  • 3a Hosokawa T. Uno T. Inui S. Murahashi SI. J. Am. Chem. Soc.  1981,  103:  2318 
    Suche in Google Scholar
  • 3b Uozumi Y. Kato K. Hayashi T. J. Am. Chem. Soc.  1997,  119:  5063 
    Suche in Google Scholar
  • 4 Tietze LF. Stecker F. Zinngrebe J. Sommer KM. Chem. Eur. J.  2006,  12:  8770 
    CrossrefSuche in Google Scholar
  • 5a Ambrosi P. Arnone A. Bravo P. Bruche L. Cristofaro AD. Francardi V. Frigerio M. Gatti E. Germinara GS. Panzeri W. Pennacchio F. Pesenti C. Rotundo G. Roversi PF. Salvadori C. Viani F. Zanda M. J. Org. Chem.  2001,  66:  8336 
    Suche in Google Scholar
  • 5b Perlmutter P. Selajerern W. Vounatsos F. Org. Biomol. Chem.  2004,  2:  2220 
    Suche in Google Scholar
  • 5c Ploysuk C. Kongkathip B. Kongkathip N. Synth. Comunun.  2007,  37:  1463 
    Suche in Google Scholar
  • This type of 6-exo-trig cyclization using aliphatic alcohols has been previously reported by Sigman and co-workers. For the related references, see:
  • 6a Schultz MJ. Sigman MS. J. Am. Chem. Soc.  2006,  128:  1460 
    Suche in Google Scholar
  • 6b Zhang Y. Sigman MS. J. Am. Chem. Soc.  2007,  129:  3076 
    Suche in Google Scholar
  • 6c Jensen KH. Pathak TP. Zhang Y. Sigman MS. J. Am. Chem. Soc.  2009,  131:  17074 
    Suche in Google Scholar
  • 6d Jensen KH. Webb JD. Sigman MS. J. Am. Chem. Soc.  2010,  132:  17471 
    Suche in Google Scholar
  • 7a Trani A. Dallanoce C. Panzone G. Ripamonti F. Goldstein BP. Ciabatti R. J. Med. Chem.  1997,  40:  967 
    Suche in Google Scholar
  • 7b Goldstein BP. King A. Ripamonti F. Trani A. Phillips I. J. Antimicrob. Chemother.  1995,  36:  1061 
    Suche in Google Scholar
  • 8a Coronell C. Pagani H. Bardone MR. Lancini GC. J. Antibiot.  1974,  27:  161 
    Suche in Google Scholar
  • 8b Puder C. Loya S. Hizi A. Zeeck A. Eur. J. Org. Chem.  2000,  729 
  • 9 Ueno T. Takahashi H. Oda M. Mizunuma M. Yokoyama A. Goto Y. Mizushina Y. Sakaguchi K. Hayashi H. Biochemistry  2000,  39:  5995 
    CrossrefPubMedSuche in Google Scholar
  • 10 Brasholz M. Sörgel S. Azap C. Reißig HU. Eur. J. Org. Chem.  2007,  3801 
  • 11a Chino M. Nishikawa K. Yamada A. Ohsono M. Sawa T. Hanaoka F. Ishizuka M. Takeuchi T. J. Antibiot.  1998,  51:  480 
    Suche in Google Scholar
  • 11b Chino M. Nishikawa K. Umekita M. Hayashi C. Yamazaki T. Tsuchida T. Sawa T. Hamada M. Takeuchi T. J. Antibiot.  1996,  49:  752 
    Suche in Google Scholar
  • 12 Goldman ME. Salituro GS. Bowen JA. Williamson JM. Zink DL. Schleif WA. Emini EA. Mol. Pharmacol.  1990,  38:  20 
    Suche in Google Scholar
  • 13a Qin D. Ren RX. Siu T. Zheng C. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4709 
    Suche in Google Scholar
  • 13b Siu T. Qin D. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4713 
    Suche in Google Scholar
  • 13c Akai S. Kakiguchi K. Nakamura Y. Kuriwaki I. Dohi T. Harada S. Kubo O. Morita N. Kita Y. Angew. Chem. Int. Ed.  2007,  46:  7458 
    Suche in Google Scholar
  • 14a Capecchi T. de Koning CB. Michael JP. Tetrahedron Lett.  1998,  39:  5429 
    Suche in Google Scholar
  • 14b Capecchi T. de Koning CB. Michael JP. J. Chem. Soc., Perkin Trans. 1  2000,  2681 
  • 14c Tsang KY. Brimble MA. Bremner JB. Org. Lett.  2003,  5:  4425 
    Suche in Google Scholar
  • 14d Tsang KY. Brimble MA. Tetrahedron  2007,  63:  6015 
    Suche in Google Scholar
  • 14e Waters SP. Fennie MW. Kozlowski MC. Tetrahedron Lett.  2006,  47:  5409 
    Suche in Google Scholar
  • 14f Waters SP. Fennie MW. Kozlowski MC. Org. Lett.  2006,  8:  3243 
    Suche in Google Scholar
  • 14g Sörgel S. Azap C. Reissig H.-U. Org. Lett.  2006,  8:  4875 
    Suche in Google Scholar
  • 15a Lindsey CC. Wu KL. Pettus TRR. Org. Lett.  2006,  8:  2365 
    Suche in Google Scholar
  • 15b For a synthesis of bisbenzannelated 6,6-spiroketals, see: Zhou G. Zheng D. Da S. Xie Z. Li Y. Tetrahedron Lett.  2006,  47:  3349 
    Suche in Google Scholar
  • 16 Zhang Y. Xue JJ. Xin ZJ. Xie ZX. Li Y. Synlett  2008,  940 
    Thieme Connect
  • 17a Qin D. Ren RX. Siu T. Zheng C. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4709 
    Suche in Google Scholar
  • 17b Siu T. Qin D. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4713 
    Suche in Google Scholar
  • 17c Akai S. Kakiguchi K. Nakamura Y. Kuriwaki I. Dohi T. Harada S. Kubo O. Morita N. Kita Y. Angew. Chem. Int. Ed.  2007,  46:  7458 
    Suche in Google Scholar
  • 17d Rathwell DCK. Yang SH. Tsang KY. Brimble MA. Angew. Chem. Int. Ed.  2009,  48:  7996 
    Suche in Google Scholar
  • 18a Smith ND. Kocienski PJ. Street SDA. Synthesis  1996,  652 
  • 18b Charette AB. Lebel H. J. Am. Chem. Soc.  1996,  118:  10327 
    Suche in Google Scholar
  • 18c Blakemore PR. Cole WJ. Kocienski PJ. Morley A. Synlett  1998,  26 
  • 19 Hosokawa T. Ohta T. Kanayama S. Murahashi SI. J. Org. Chem.  1987,  52:  1758 
    Suche in Google Scholar