Catalyst-Free, Direct, High Regio- and Chemoselective Conversion of Epoxides to Vicinal Haloesters Under Mild, Neutral, and Solvent-Free Conditions

REFERENCES

• Behrens , C. H. ; Ko , S. Y. ; Sharpless , K. B. ; Walker , F. J. Selective transformation of 2,3-epoxy alcohols and related derivatives: Strategies for nucleophilic attack at carbon-1 . J. Org. Chem. 1985 , 50 , 5687 – 5696 .
   Web of Science ®Google Scholar
• Nugent , W. A. Chiral Lewis acid catalysis: Enantioselective addition of azide to meso epoxides . J. Am. Chem. Soc. 1992 , 114 , 2768 – 2769 .
   Web of Science ®Google Scholar
• Tokunaga , M. ; Larrow , J. F. ; Kakiuchi , F. ; Jacobsen , E. N. Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis . Science 1997 , 277 , 936 – 938 .
   PubMed Web of Science ®Google Scholar
• Bonini , C. R. ; Righi , G. Regio- and chemoselective synthesis of halohydrins by cleavage of oxiranes with metal halides . Synthesis 1994 , 225 – 238 .
   Web of Science ®Google Scholar
• Smith , J. G. Synthetically useful reactions of epoxides . Synthesis 1984 , 629 – 656 .
   Web of Science ®Google Scholar
• Yamada , J. ; Yumoto , M. ; Yamamoto , Y. Aminolead compounds as a new reagent for regioselective ring opening of epoxides . Tetrahedron Lett. 1989 , 30 , 4255 – 4258 .
   Web of Science ®Google Scholar
• (a) Konopelski , J. P. ; Boehler , M. A. ; Tarasow , T. M. Preparation of (1R,2S)- and (1S,2R)-2-chloro-1,2-diphenylethanol and other. β-halohydrins in enantiomerically pure form . J. Org. Chem. 1989 , 54 , 4966 – 4970 ; (b) Ueda , Y. ; Maynard , S. C. Highly regioselective formation of bromohydrins by reaction of epoxy-azetidinones with MgBr2: An alternative route to 4-bromomethylcarbonylmethyl-2-azetidinone, a key carbapenem precursor . Tetrahedron Lett. 1988 , 29 , 5197 – 5200 .
   Web of Science ®Google Scholar
• (a) Iranpoor , N. ; Firouzabadi , H. ; Aghapour , G. ; Nahid , A. Selective conversion of epoxides to vic-halo alcohols and symmetrical or unsymmetrical dihalides by triphenylphosphine/2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in the presence of quaternary ammonium halides . Bull. Chem. Soc. Jpn. 2004 , 77 , 1885 – 1891 ; (b) Iranpoor , N. ; Adibi , H. Iron(III) trifluoroacetate as an efficient catalyst for solvolytic and nonsolvolytic nucleophilic ring opening of epoxides . Bull. Chem. Soc. Jpn. 2000 , 73 , 675 – 680 ; (c) Garrett , C. E. ; Fu , G. C. π-Bound phosphorus heterocycles as catalysts: Ring opening of epoxides with TMSCl in the presence of a phosphaferrocene . J. Org. Chem. 1997 , 62 , 4534 – 4535 ; (d) Kotsuki , H. ; Shimanouchi , T. ; Ohshima , R. ; Fujiwara , S. Solvent-free organic reactions on silica-gel supports: Facile transformation of epoxides to β-halohydrins with lithium halides . Tetrahedron 1998 , 54 , 2709 – 2722 ; (e) Kwon , D. W. ; Cho , M. S. ; Kim , Y. H. Samarium(III) iodide complex catalyzed regioselective cleavage of epoxides to iodohydrins: tandem epoxide opening–iodocyclization . Synlett 2003 , 959 – 962 .
   Web of Science ®Google Scholar
• (a) Shaghi , H. ; Eskandari , M. M. Conversion of epoxides to halohydrins with elemental halogen catalyzed by phenylhydrazine. Synthesis 2002, 1519–1522; (b) Shaghi , H. ; Massah , A. R. ; Eshghi , H. ; Niknam , K. Crown ethers as new catalysts in the highly regioselective halogenative cleavage of epoxides with elemental halogen. J. Org. Chem. 1998, 63, 1455–1461; (c) Diaz , D. ; Martin , T. ; Martin , V. S. Stereocontrolled synthesis of unsaturated halohydrins from unsaturated epoxides. J. Org. Chem. 2001, 66, 7231–7233; (d) Aghapour , G. ; Afzali , A. ; Salek , F. Facile, high regio- and chemoselective conversion of epoxides to β-chlorohydrins using chloro diphenyl phosphine under solvent-free conditions. Indian J. Chem. 2009, 48B, 231–236.
   Google Scholar
• Otera , J. Esterification, Methods, Reactions, And Applications ; Wiley-VCH Verlag : Weinheim , 2003 .
   Google Scholar
• (a) Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis ; Wiley : New York , 1991 ; (b) Kocienski , P. J. Protecting Groups ; Thieme : Stuttgart , 1994 .
   Google Scholar
• Larock , R. C. Comprehensive Organic Transformations ; VCH : New York , 1989 ; p. 980 ; For more references see: (a) Saravanan , P. ; Singh , V. K. An efficient method for acylation reactions. Tetrahedron Lett. 1999, 40, 2611–2614; (b) Chandrasekhar , S. ; Ramachander , T. ; Takhi , M. Acylation of alcohols with acetic anhydride catalyzed by TaCl5: Some implications in kinetic resolution. Tetrahedron Lett. 1998, 39, 3263–3266; (c) Damen , E. W. P. ; Braamer , L. ; Scheeren , H. W. Lanthanide trifluoromethanesulfonate–catalysed selective acylation of 10-deacetylbaccatin III. Tetrahedron Lett. 1998, 39, 6081–6082; (d) Orita , A. ; Mitsutome , A. ; Otera , J. Distannoxane-catalyzed highly selective acylation of alcohols. J. Org. Chem. 1998, 63, 2420–2421; (e) Breton , G. W. Selective monoacetylation of unsymmetrical diols catalyzed by silica gel–supported sodium hydrogen sulfate. J. Org. Chem. 1997, 62, 8952–8954; (f) Orita , A. ; Sakamoto , K. ; Hamada , Y. ; Mitsutome , A. ; Otera , J. Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis. Tetrahedron 1999, 55: 2899–2910 .
   Google Scholar
• (a) Li , T. S. ; Li , A. X. Montmorillonite clay catalysis, part 10: K-10 and KSF-catalysed acylation of alcohols, phenols, thiols and amines: Scope and limitation . J. Chem. Soc., Perkin Trans. 1998 , 1 , 1913 – 1918 ; (b) Ballini , R. ; Bosica , G. ; Carloni , L. ; Ciaralli , L. ; Maggi , R. ; Sartori , G. Zeolite HSZ-360 as a new reusable catalyst for the direct acetylation of alcohols and phenols under solventless conditions . Tetrahedron Lett. 1998 , 39 , 6049 – 6052 ; (c) Bhaskar , P. M. ; Loganathan , D. Per-O-acetylation of sugars catalysed by montmorillonite K-10 . Tetrahedron Lett. 1998 , 39 , 2215 – 2218 .
   Google Scholar
• (a) Williams , J. R. ; Boehm , J. C. The syntheses of 3 beta-steroidal diacylglyceryl sulfides, sulfoxides, and sulfones . Steroids 1995 , 60 , 321 – 323 ; (b) Junk , T. ; Pappalardo , G. C. ; Irgolic , K. J. Synthesis and characterization of rac-1,2-bis(palmitoyloxy)-3-propyl (2-trimethylarsonioethyl)phosphonate, an arsenic-containing phosphonolipid . Appl. Organomet. Chem. 1990 , 4 , 103 – 109 ; (c) Lok , C. M. Versatile methods for the synthesis of mixed-acid 1,2-diacylglycerols . Chem. Phys. Lipids 1978 , 22 , 323 – 337 ; (d) Ali , S. ; Bittman , R. Facile diacylation of glycidyl tosylate: Chiral synthesis of symmetric-chain glycerophospholipids . J. Org. Chem. 1988 , 53 , 5547 – 5549 .
   PubMed Web of Science ®Google Scholar
• Prades , J. ; Funari , S. S. ; Escriba , P. V. ; Barcelo , F. Effects of unsaturated fatty acids and triacylglycerols on phosphatidylethanolamine membrane structure . J. Lipid Res. 2003 , 44 , 1720 – 1727 .
   PubMed Web of Science ®Google Scholar
• (a) Iwasaki , Y. ; Yamane , T. Enzymatic synthesis of structured lipids . J. Mol. Catal. B: Enzym. 2000 , 10 , 129 – 140 ; (b) Pleiss , J. ; Scheib , H. ; Schmid , R. D. The His gap motif in microbial lipases: A determinant of stereoselectivity toward triacylglycerols and analogs . Biochimie 2000 , 82 , 1043 – 1052 .
   Web of Science ®Google Scholar
• Ren , T. ; Liu , D. Synthesis of cationic lipids from 1,2,4-butanetriol . Tetrahedron Lett. 1999 , 40 , 209 – 212 .
   Web of Science ®Google Scholar
• (a) Kurz , M. ; Scriba , G. K. E. Drug–phospholipid conjugates as potential prodrugs: Synthesis, characterization, and degradation by pancreatic phospholipase A2 . Chem. Phys. Lipids 2000 , 107 , 143 – 157 ; (b) Parang , K. ; Wiebe , L. I. ; Knaus , E. E. Novel approaches for designing 5′-O-ester prodrugs of 3′-azido-2′3′-dideoxythymidine (AZT) . Curr. Med. Chem. 2000 , 7 , 995 – 1039 .
   PubMed Web of Science ®Google Scholar
• Bajwa , J. S. ; Anderson , R. C. A highly regioselective conversion of epoxides to halohydrins by lithium halides. Tetrahedron Lett. 1991, 32, 3021–3024.
   Web of Science ®Google Scholar
• Parfenov , E. A. ; Serebrennikova , G. A. ; Preobrazhenskii , N. A. Zh. Org. Khim. 1967 , 3 , 1951 – 1955 .
   Google Scholar
• (a) Sharpless , K. B. ; Teranishi , A. Y. ; Backvall , J. E. Chromyl chloride oxidations of olefins: Possible role of organometallic intermediates in the oxidations of olefins by oxo transition metal species . J. Am. Chem. Soc. 1977 , 99 , 3120 – 3128 . (b) Backvall , J. E. ; Young , M. W. ; Sharpless , K. B. Vicinal acetoxychlorination of olefins by chromyl chloride in acetyl chloride . Tetrahedron Lett. 1977 , 18 , 3523 – 3526 .
   Web of Science ®Google Scholar
• Iqbal , J. ; Amin Khan , M. ; Srivastava , R. R. Cobalt-catalysed regioselective cleavage of oxiranes with acylchlorides . Tetrahedron Lett. 1988 , 29 , 4985 – 4986 .
   Web of Science ®Google Scholar
• Shibata , I. ; Baba , A. ; Matsuda , H. Regioselective ring cleavage of oxiranes catalyzed by organotin halide–triphenylphosphine complex . Tetrahedron Lett. 1986 , 27 , 3021 – 3024 .
   Web of Science ®Google Scholar
• Gros , P. ; Le Perchec , P. ; Senet , J. P. Reaction of epoxides with chlorocarbonylated compounds catalyzed by hexaalkylguanidinium chloride . J. Org. Chem. 1994 , 59 , 4925 – 4930 .
   Web of Science ®Google Scholar
• Azizi , N. ; Mirmashhori , B. ; Saidi , M. R. Lithium perchlorate–promoted highly regioselective ring opening of epoxides under solvent-free conditions . Catal. Commun. 2007 , 8 , 2198 – 2203 .
   Web of Science ®Google Scholar
• Iranpoor , N. ; Zeynizadeh , B. Efficient and regioselective conversion of epoxides into vicinal chloroesters with TiCl4 and imidazole in ethyl acetate . J. Chem. Res. Synop. 1998 , 582 – 583 .
   Web of Science ®Google Scholar
• Stamatov , S. D. ; Stawinski , J. Efficient, highly regioselective, and stereospecific conversion of glycidol systems into C2-O-acylated vicinal halohydrins . Tetrahedron Lett. 2006 , 47 , 2543 – 2547 .
   Web of Science ®Google Scholar
• Oriyama , T. ; Ishiwata , A. ; Hori , Y. ; Yatabe , T. ; Hasumi , N. ; Koga , G. Highly regioselective tin-mediated ring opening of 2,3-epoxy alcohol derivatives with trimethylisilyl halide . Synlett 1995 , 1004 – 1006 .
   Web of Science ®Google Scholar
• Tanaka , K. Solvent-Free Organic Synthesis ; Wiley-VCH Verlag : Weinheim , 2003 .
   Google Scholar
• Tanaka , K. ; Toda , F. Solvent-free organic synthesis . Chem. Rev. 2000 , 100 , 1025 – 1074 .
   PubMed Web of Science ®Google Scholar
• (a) Aghapour , G. ; Hatefipour , R. Catalyst-free, efficient, and facile conversion of epoxides to β-hydroxy thiocyanates under neutral conditions . Synth. Commun. 2009 , 39 , 1698 – 1707 . (b) Aghapour , G. ; Afzali , A. Solvent-free, efficient, and high regioselective conversion of epoxides to symmetrical and unsymmetrical vic-dihalides using chlorodiphenylphosphine and N-halosuccinimides . Phosphorus, Sulfur Silicon Relat. Elem. 2011 , 186 ( 3 ): 598 – 605 .
   Google Scholar
• Aghapour , G. ; Hatefipour , R. Catalyst-free, direct, high regio-, and chemo-selective conversion of epoxides to 2-thiocyanatoalkyl alkanoates under neutral and solvent-free conditions . Can. J. Chem. 2010 , 88 ( 7 ), 598 – 604 .
   Web of Science ®Google Scholar
• Winstein , S. ; Buckles , R. E. The role of neighboring groups in replacement reactions, I: Retention of configuration in the reaction of some dihalides and acetoxyhalides with silver acetate . J. Am. Chem. Soc. 1942 , 64 , 2780 – 2786 .
   Web of Science ®Google Scholar
• Taniguchi , Y. ; Tanaka , S. ; Kitamura , T. ; Fujiwara , Y. Lanthanoid-catalyzed ring-opening reaction of epoxides with acyl halides . Tetrahedron Lett. 1998 , 39 , 4559 – 4560 .
   Web of Science ®Google Scholar