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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 20
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Original Articles

Selective Synthesis of β‐Hydroxy Nitroethanol Ethers by Alcoholysis of Oxiranes

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Pages 3589-3598 | Received 05 Oct 2006, Published online: 05 Oct 2007

References

  • Fringuelli , F. , Pizzo , F. , Vittoriani , C. and Vaccaro , L. 2004 . Polystyryl‐supported TBD as an efficient and reusable catalyst under solvent‐free conditions . Chem. Commun. , : 2756 – 2757 .
  • Malinovskii , M. S. , Korchagina , A. M. , Yudasina , A. G. , Zinovkina , V. A. and Demchenko , T. V. β‐Hydroxy nitro ethers . U.S.S.R. patent .
  • Boynton , J. A. , Hanson , J. R. and Uyanik , C. 1995 . Stereochemistry of the tetracyanoethylene‐catalyzed methanolysis of steroidal epoxides . J. Chem. Res., Synop. , : 334 – 335 .
  • Iranpoor , N. and Baltork , I. M. 1990 . Mild, efficient and selective opening of epoxides with alcohols catalyzed by ceric(IV) ammonium nitrate . Synth. Commun. , 20 : 2789 – 2797 .
  • Iranpoor , N. , Mohammadpour‐Baltork , I. and Zardaloo , F. S. 1991 . Ceric ammonium nitrate, an efficient catalyst for mild and selective opening of epoxides in the presence of water thiols and acetic acid . Tetrahedron , 47 : 9861 – 9866 .
  • Iranpoor , N. and Mohammadpour‐Baltork , I. 1990 . 2,3‐Dichloro‐5,6‐dicyano‐p‐benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxides . Tetrahedron Lett. , 31 : 735 – 738 .
  • Han , J. H. , Hong , S. J. , Lee , E. Y. , Lee , J. H. , Kim , H. J. , Kwak , H. and Kim , C. 2005 . Conversion of epoxides into trans‐diols or trans‐diol mono ethers by iron(III) porphirin complexe . Bull. Korean Chem. Soc. , 26 : 1434 – 1436 .
  • Iranpoor , N. and Adibi , H. 2000 . Iron(III) trifluoroacetate as an efficient catalyst for solvolytic and nonsolvolytic nucleophilic ring opening of epoxides . Bull. Chem. Soc. Jpn. , 73 : 675 – 680 .
  • Mohammadpoor‐Baltork , I. , Tangestaninejad , S. , Aliyan , H. and Mirkhani , V. 2000 . Bismuth(III) chloride (BiCl3), an efficient catalyst for mild, region‐ and stereoselective cleavage of epoxides with alcohols, acetic acid and water . Synth. Commun. , 30 : 2365 – 2374 .
  • Ready , J. M. and Jacobsen , E. N. 2001 . Highly active oligomeric (salen)Co catalysts for asymmetric epoxide ring‐opening reactions . J. Am. Chem. Soc. , 123 : 2687 – 2688 .
  • Likhar , P. R. , Kumar , M. P. and Bandyopadhyay , A. K. 2001 . Ytterbium trifluoromethanesulfonate Yb(OTf)3, an efficient, reusable catalyst for highly selective formation of β‐alkoxy alcohols via ring‐opening of 1,2‐epoxides with alcohols . Synlett , : 836 – 838 .
  • Schneider , C. , Sreekanth , A. R. and Mai , E. 2004 . Scandium‐bipyridine‐catalyzed enantioselective addition of alcohols and amines to meso‐epoxides . Angew. Chem. Int. Ed. , 43 : 5691 – 5694 .
  • Boyer , F.‐D. and Hanna , I. 2005 . Remarkable selectivity in addition of alcohols to epoxydienes of 5,7‐bicyclic and 5,7‐tricyclic systems . J. Org. Chem. , 70 : 1077 – 1080 .
  • Barluenga , J. , Vazquez‐Villa , H. , Ballesteros , A. and Gonzalez , J. M. 2002 . Copper(II) tetrafluoroborate catalyzed ring‐opening reaction of epoxides with alcohols at room temperature . Org. Lett. , 4 : 2817 – 2819 .
  • Salomon , C. J. 2001 . Bis‐chlorodibutyltin oxide as a new reagent for a mild, versatile and regioselective ring‐opening of epoxides . Synlett , : 65 – 68 .
  • Malinovskii , M. S. , Yudasina , A. G. and Korchagina , A. M. 1968 . Interaction of ethylene oxide with nitro alcohols . Ukr. Khim. Zh. (Russ. Ed.) , 34 : 489 – 491 .
  • Malinovskii , M. S. , Korchagina , A. M. , Yudasina , A. G. and Zinovkina , V. A. 1973 . Reaction of α‐oxides with 1‐nitro‐2‐ethanol . Ukr. Khim. Zh. (Russ. Ed.) , 39 : 365 – 368 .
  • Fokin , A. V. , Komarov , V. A. , Voronkov , A. N. , Shevchenko , V. I. and Lyubimova , E. I. 1975 . Difluoronitroethyl ethers of 1,2‐alkylilene glycols and their derivatives . Izv. Akad. Nauk SSSR, Ser. Khim. , : 1448 – 1450 .
  • Masaki , Y. , Miura , T. and Ochiai , M. 1993 . Alcoholysis of epoxides catalyzed by tetracyanoethylene . Synlett , : 847 – 849 .
  • Masaki , Y. , Miura , T. and Ochiai , M. 1996 . Alcoholysis of epoxides catalyzed by tetracyanoethylene and dicyanoketene acetals . Bull. Chem. Soc. Jpn. , 69 : 195 – 205 .
  • Collado , I. G. , Hanson , J. R. and Macias‐Sanchez , A. J. 1996 . The cleavage of caryophyllene oxide catalyzed by tetracyanoethylene . Tetrahedron , 52 : 7961 – 7972 .
  • Hanson , J. R. , Macias‐Sanchez , A. J. and Uyanik , C. 2001 . Applications of tetracyanoethylene as a π‐acid catalyst . J. Chem. Res., Synop. , 121–123 : 0401 – 0410 .

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