Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 8
93
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

FeCl3 · 6H2O-Catalyzed Bromocyclization to Access Functionalized Dihydropyrans

, , &
Pages 1227-1238 | Received 12 Mar 2010, Published online: 21 Mar 2011

REFERENCES

  • (a) Dzudza , A. ; Marks , T. J. Efficient intramolecular hydroalkoxylation/cyclization of unactivated alkenols mediated by lanthanide triflate ionic liquids . Org. Lett. 2009 , 11 , 1523 – 1526 ; (b) Gockel , B. ; Krause , N. Golden times for allenes: Gold-catalyzed cycloisomerization of β-hydroxyallenes to dihydropyrans . Org. Lett. 2006 , 8 , 4485 – 4488 ; (c) Yadav , V. K. ; Kumar , N. V. Highly stereoselective Prins cyclization of silylmethyl-substituted cyclopropyl carbinols to 2,4,6-trisubstituted tetrahydropyrans . J. Am. Chem. Soc. 2004 , 126 , 8652 – 8653 ; (d) Nicolaou , K. C. ; Sorensen , E. J. Classics in Total Synthesis; VCH: Weinheim, 1996 .
  • (a) Yadav , J. S. ; Sunitha , V. ; Subba , B. V. ; Das , P. P. ; Gyanchander , E. InBr3-catalyzed stereoselective synthesis of trans-2,6-disubstituted 3,6-dihydro-2H-pyrans . Tetrahedron Lett. 2008 , 49 , 855 – 857 ; (b) Class , Y. J. ; Deshong , P. The pseudomonic acids . Chem. Rev. 1995 , 95 , 1843 – 1857 ; (c) Faulkner , D. J. Marine natural products . Nat. Prod. Rep. 2000 , 17 , 7 – 55 .
  • (a) Pellissier , H. Asymmetric hetero-Diels–Alder reactions of carbonyl compounds. Tetrahedron 2009, 65, 2839–2877; (b) Dintzner , M. R. ; Little , A. J. ; Pacilli , M. ; Pileggi , D. J. ; Osner , Z. R. ; Lyons , T. W. Montmorillonite clay-catalyzed hetero-Diels–Alder reaction of 2,3-dimethyl-1,3-butadiene with benzaldehydes. Tetrahedron Lett. 2007, 48, 1577–1579.
  • (a) Miranda , P. O. ; Carballo , R. M. ; Martín , V. S. ; Padrón , J. I. A new catalytic Prins cyclization leading to oxa- and azacycles . Org. Lett. 2009 , 11 , 357 – 360 ; (b) Hu , X. H. ; Liu , F. ; Loh , T. P. Stereoelectronic versus steric tuning in the Prins cyclization reaction: Synthesis of 2,6-trans pyranyl motifs . Org. Lett. 2009 , 11 , 1741 – 1743 ; (c) Miranda , P. O. ; Ramírez , M. A. ; Martín , V. S. ; Padrón , J. I. Factors controlling the alkyne Prins cyclization: The stability of dihydropyranyl cations . Chem. Eur. J. 2008 , 14 , 6260 – 6268 ; (d) Dziedzic , M. ; Furman , B. An efficient approach to the stereoselective synthesis of 2,6-disubstituted dihydropyrans via stannyl-Prins cyclization . Tetrahedron Lett. 2008 , 49 , 678 – 681 .
  • (a) Xie , M. H. ; Wang , J. L. ; Zhang , W. ; Wang , S. W. Regio- and stereospecific synthesis of vinyl halides via carbozincation of acetylenic sulfones followed by halogenations . J. Organomet. Chem. 2009 , 694 , 2258 – 2262 ; (b) Lebrun , M. E. ; Marquand , P. L. ; Berthelette , C. Stereoselective synthesis of Z alkenyl halides via Julia olefination . J. Org. Chem. 2006 , 71 , 2009 – 2013 ; (c) Jereb , M. ; Jupan , M. ; Stavber , S. Hydrogen peroxide–induced iodine transfer into alkenes . Green Chem. 2005 , 7 , 100 – 104 .
  • (a) Arimitsu , S. ; Jacobsen , J. M. ; Hammond , G. B. Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols . J. Org. Chem. 2008 , 73 , 2886 – 2889 ; (b) Chen , J. ; Lu , L. H. ; Ma , S. M. Studies on the factors controlling the stereoselectivity in electrophilic iodocyclization of alkylidenecyclopropyl ketones . Tetrahedron 2008 , 64 , 8899 – 8906 ; (c) Lee , A. S. Y. ; Tsao , K. W. ; Chang , Y. T. ; Chu , S. F. L-Proline-catalyzed intramolecular cyclization of 5-hydroxypentene to β-halogenated tetrahydrofuran . Tetrahedron Lett. 2007 , 48 , 6790 – 6793 ; (d) Knight , D. W. ; Rost , H. C. ; Sharland , C. M. ; Singkhonrat , J. A general approach to polysubstituted pyrroles . Tetrahedron Lett. 2007 , 48 , 7906 – 7910 .
  • (a) Liu , Z. Q. ; Wang , J. G. ; Han , J. ; Zhao , Y. K. ; Zhou , B. An efficient and mild iron-mediated synthesis of alkenyl halides via direct C‒C bond formation of benzyl alcohols and aryl alkynes . Tetrahedron Lett. 2009 , 50 , 1240 – 1242 ; (b) Sherry , B. D. ; Fürstner , A. The promise and challenge of iron-catalyzed cross coupling . Acc. Chem. Res. 2008 , 41 , 1500 – 1511 ; (c) Carril , M. ; Correa , A. ; Bolm , C. Iron-catalyzed Sonogashira reactions . Angew. Chem. Int. Ed. 2008 , 47 , 4862 – 4865 ; (d) Huang , W. ; Zheng , P. Z. ; Zhang , Z. X. ; Liu , R. T. ; Chen , Z. X. ; Zhou , X. G. Controllable one-step synthesis of spirocycles, polycycles, and di- and tetrahydronaphthalenes from aryl-substituted propargylic alcohols . Org. Lett. 2008 , 73 , 6845 – 6848 ; (e) Bolm , C. ; Legros , J. ; Paih , J. L. ; Zani , L. Iron-catalyzed reactions in organic synthesis . Chem. Rev. 2004 , 104 , 6217 – 6254 .
  • Xie , M. H. ; Liu , L. ; Wang , J. L. ; Wang , S. W. Stereoselective synthesis of vinyl sulfones by carbomagnesiation of acetylenic sulfone in the presence of CuCN . J. Organomet. Chem. 2005 , 690 , 4058 – 4062 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.