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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;
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Publication History

Received 7 March 2011
Publication Date:
10 June 2011 (online)

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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 
    Google Scholar
  • 2 Korotchenko VN. Gagne MR. J. Org. Chem.  2007,  72:  4877 
    CrossrefGoogle Scholar
  • 3a Hosokawa T. Uno T. Inui S. Murahashi SI. J. Am. Chem. Soc.  1981,  103:  2318 
    Google Scholar
  • 3b Uozumi Y. Kato K. Hayashi T. J. Am. Chem. Soc.  1997,  119:  5063 
    Google Scholar
  • 4 Tietze LF. Stecker F. Zinngrebe J. Sommer KM. Chem. Eur. J.  2006,  12:  8770 
    CrossrefGoogle 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 
    Google Scholar
  • 5b Perlmutter P. Selajerern W. Vounatsos F. Org. Biomol. Chem.  2004,  2:  2220 
    Google Scholar
  • 5c Ploysuk C. Kongkathip B. Kongkathip N. Synth. Comunun.  2007,  37:  1463 
    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 
    Google Scholar
  • 6b Zhang Y. Sigman MS. J. Am. Chem. Soc.  2007,  129:  3076 
    Google Scholar
  • 6c Jensen KH. Pathak TP. Zhang Y. Sigman MS. J. Am. Chem. Soc.  2009,  131:  17074 
    Google Scholar
  • 6d Jensen KH. Webb JD. Sigman MS. J. Am. Chem. Soc.  2010,  132:  17471 
    Google Scholar
  • 7a Trani A. Dallanoce C. Panzone G. Ripamonti F. Goldstein BP. Ciabatti R. J. Med. Chem.  1997,  40:  967 
    Google Scholar
  • 7b Goldstein BP. King A. Ripamonti F. Trani A. Phillips I. J. Antimicrob. Chemother.  1995,  36:  1061 
    Google Scholar
  • 8a Coronell C. Pagani H. Bardone MR. Lancini GC. J. Antibiot.  1974,  27:  161 
    Google Scholar
  • 8b Puder C. Loya S. Hizi A. Zeeck A. Eur. J. Org. Chem.  2000,  729 
    Google Scholar
  • 9 Ueno T. Takahashi H. Oda M. Mizunuma M. Yokoyama A. Goto Y. Mizushina Y. Sakaguchi K. Hayashi H. Biochemistry  2000,  39:  5995 
    CrossrefPubMedGoogle Scholar
  • 10 Brasholz M. Sörgel S. Azap C. Reißig HU. Eur. J. Org. Chem.  2007,  3801 
    Google Scholar
  • 11a Chino M. Nishikawa K. Yamada A. Ohsono M. Sawa T. Hanaoka F. Ishizuka M. Takeuchi T. J. Antibiot.  1998,  51:  480 
    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 
    Google Scholar
  • 12 Goldman ME. Salituro GS. Bowen JA. Williamson JM. Zink DL. Schleif WA. Emini EA. Mol. Pharmacol.  1990,  38:  20 
    Google Scholar
  • 13a Qin D. Ren RX. Siu T. Zheng C. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4709 
    Google Scholar
  • 13b Siu T. Qin D. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4713 
    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 
    Google Scholar
  • 14a Capecchi T. de Koning CB. Michael JP. Tetrahedron Lett.  1998,  39:  5429 
    Google Scholar
  • 14b Capecchi T. de Koning CB. Michael JP. J. Chem. Soc., Perkin Trans. 1  2000,  2681 
    Google Scholar
  • 14c Tsang KY. Brimble MA. Bremner JB. Org. Lett.  2003,  5:  4425 
    Google Scholar
  • 14d Tsang KY. Brimble MA. Tetrahedron  2007,  63:  6015 
    Google Scholar
  • 14e Waters SP. Fennie MW. Kozlowski MC. Tetrahedron Lett.  2006,  47:  5409 
    Google Scholar
  • 14f Waters SP. Fennie MW. Kozlowski MC. Org. Lett.  2006,  8:  3243 
    Google Scholar
  • 14g Sörgel S. Azap C. Reissig H.-U. Org. Lett.  2006,  8:  4875 
    Google Scholar
  • 15a Lindsey CC. Wu KL. Pettus TRR. Org. Lett.  2006,  8:  2365 
    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 
    Google Scholar
  • 16 Zhang Y. Xue JJ. Xin ZJ. Xie ZX. Li Y. Synlett  2008,  940 
    Article in Thieme ConnectGoogle Scholar
  • 17a Qin D. Ren RX. Siu T. Zheng C. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4709 
    Google Scholar
  • 17b Siu T. Qin D. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4713 
    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 
    Google Scholar
  • 17d Rathwell DCK. Yang SH. Tsang KY. Brimble MA. Angew. Chem. Int. Ed.  2009,  48:  7996 
    Google Scholar
  • 18a Smith ND. Kocienski PJ. Street SDA. Synthesis  1996,  652 
    Google Scholar
  • 18b Charette AB. Lebel H. J. Am. Chem. Soc.  1996,  118:  10327 
    Google Scholar
  • 18c Blakemore PR. Cole WJ. Kocienski PJ. Morley A. Synlett  1998,  26 
    Google Scholar
  • 19 Hosokawa T. Ohta T. Kanayama S. Murahashi SI. J. Org. Chem.  1987,  52:  1758 
    Google Scholar