One-Pot System for Reduction of Epoxides Using NaBH₄, PdCl₂ Catalyst, and Moist Alumina

REFERENCES

• (a) Bauer , K. ; Garbe , D. ; Surburg , H. Common Fragrance; and Flavor Materials ; VHC : New York , 1990 ; (b) Theimer , E. T. Fragrance Chemistry ; Academic Press : New York , 1982 ; p. 271 ; (c) Mookherjee , B. D. ; Wilson , R. A. (Eds.). Kirk-Othmer Encyclopedia of Chemical Technology, , 4th ed. , vol. 4 ; John Wiley and Sons : New York , 1996 .
   Google Scholar
• (a) Penne , J. S. Reductions by the Alumino- and Borohydrides in Organic Synthesis, , 2nd ed. ; Wiley-VCH : New York , 1997 ; (b) Hudlicky, M. Reductions in Organic Synthesis; American Chemical Society: Washington, DC, 1996; (c) Burke, S. D.; Danheiser, R. L. (Eds.). Handbook of Reagents for Organic Synthesis: Oxidizing; and Reducing Agents; John Wiley; & Sons: Chichester, UK, 1999; p. 394; (d) Khosropour, A. R.; Khodaei, M. M.; Ghozati, K. Bi(OTf)3- and Bi(TFA)3-catalyzed ring opening of epoxides with anilines under microwave irradiation. Chem. Lett. 2004, 33, 304 .
   Google Scholar
• (a) House , H. O. Modern Synthetic Reactions ; W. A. Benjamin : Menlo Park, CA , 1972 ; ch. 1 – 4 ; (b) Hutchins, R. O.; Taffer, I. M.; Burgoyne, W. Regio- and stereoselective cleavage of epoxides with cyanoborohydride and boron trifluoride etherate. J. Org. Chem. 1981, 46, 5214; (c) Brown, H. C.; Yoon, N. M. The borohydride-catalyzed reaction of diborane with epoxides: The anti-Markovnikov opening of trisubstituted epoxides. J. Am. Chem. Soc. 1968, 90, 2686 .
   Google Scholar
• Ranu , B. C. ; Das , A. R. Regio- and stereo-selective reductive cleavage of epoxides with zinc borohydride supported on silica gel . J. Chem. Soc., Chem. Commun. 1990 , 1334 .
   Google Scholar
• Campelo , J. M. ; Chakraborty , R. ; Marinas , J. M. Reductive cleavage of epoxides with zinc borohydride supported on ALPO4 . Synth. Commun. 1996 , 26 , 415 .
   Web of Science ®Google Scholar
• Tewari , B. B. ; Shekar , S. ; Huang , L. ; Gorrell , C. E. ; Murphy , T. P. ; Warren , K. ; Nesnas , N. ; Wehmschulte , R. J. Aluminumoxyhydride: Improved synthesis and application as a selective reducing agent . Inorg. Chem. 2006 , 45 , 8807 .
   PubMed Web of Science ®Google Scholar
• (a) Yakabe , S. ; Hirano , M. ; Clark , J. H. ; Morimoto , T. Simple reduction of various ketones with sodium tetrahydroborate and alumina in hexane . J. Chem. Res., Synop. 1998 , 322 ; (b) Yakabe , S. ; Hirano , M. ; Morimoto , T. Alumina-assisted reduction of carbonyl compounds with sodium borohydride in hexane . Can. J. Chem. 1998 , 76 , 1916 .
   Web of Science ®Google Scholar
• (a) Kamal , A. ; Shaik , A. A. ; Sandbhor , M. ; Malik , S. Synthesis of enantiopure β-azidoalcohols from their ketoazides by reduction with NaBH4 in the presence of alumina and in situ lipase resolution. Tetrahedron: Asymmetry 2004, 15, 935; (b) Kamal , A. ; Sandbhor , M. ; Ahmad , K. ; Adil , S. F. ; Shaik , A. A. Chemoenzymatic synthesis of enantiomerically pure terminal 1,2-diols. Tetrahedron: Asymmetry 2003, 14, 3861; (c) Kamal , A. ; Sandbhor , M. ; Shaik , A. A. ; Sravanthi , V. One-pot synthesis and resolution of chiral allylic alcohols. Tetrahedron: Asymmetry 2003, 14, 2839; (d) Kamal , A. ; Sandbhor , M. ; Shaik , A. A. Application of a one-pot lipase resolution strategy for the synthesis of chiral γ- and δ-lactones. Tetrahedron: Asymmetry 2003, 14, 1575; (e) Kamal , A. ; Sandbhor , M. ; Ramana , K. V. One-pot lipase-catalyzed synthesis of enantiopure secondary alcohols from carbonyl compounds: A new protocol for lipase-mediated resolution. Tetrahedron: Asymmetry 2002, 13, 815; (f) Kamal , A. ; Sandbhor , M. Efficient chemoenzymatic synthesis of (S)- and (R)-5-(1-aminoethyl)-2-(cyclohexylmethoxy)benzamide: Key intermediate for Src-SH2 inhibitor. Bioorg. Med. Chem. Lett. 2002, 12, 1735.
   Google Scholar
• Yakabe , S. ; Hirano , M. ; Morimoto , T. Hydrogenation of alkenes with sodium borohydride and moist alumina catalyzed by nickel chloride . Tetrahedron Lett. 2000 , 41 , 6795 .
   Web of Science ®Google Scholar
• Clark , J. H. ; Kybett , A. P. ; Macquarrie , D. J. Supported Reagents: Preparation, Analysis, and Application ; VCH : New York , 1992 .
   Google Scholar
• (a) Sikhwivhilu , L. M. ; Covile , N. J. ; Pulimaddi , B. M. ; Venkatreddy , J. ; Vishwanathan , V. Selective hydrogenation of o-chloronitrobenzene over palladium-supported nanotubular titanium dioxide deriver catalysts . Catal. Commun. 2007 , 8 , 1999 ; (b) Shekar , S. C. ; Rao , K. S. R. ; Sahle-Demessie , E. Characterization of palladium supported on γ-Al2O3 catalysts in hydrodechlorination of CCl2F2 . App. Catal. 2005 , 294 , 235 .
   Web of Science ®Google Scholar
• (a) Eliel , E. L. ; Rerick , M. N. Reductions with metal hydrides, VII: Reduction of epoxides with lithium aluminum hydride–aluminum chloride . J. Am. Chem. Soc. 1960 , 82 , 1362 ; (b) Smith , J. G. Synthetically useful reactions of epoxides . Synthesis 1984 , 629 ; (c) Eliel , E. L. ; Delmonte , D. W. Anomalous reduction of epoxides with lithium aluminum hydride . J. Am. Chem. Soc. 1956 , 78 , 3226 .
   Web of Science ®Google Scholar
• (a) Bartmann , E. Organometallic derivatives of epoxides . Angew. Chem. Int. Ed. 1986 , 25 , 653 ; (b) Sajiki , H. ; Hattori , K. ; Hirota , K. Pd/C(en)-catalyzed regioselective hydrogenolysis of terminal epoxides to secondary alcohols . Chem. Commun. 1999 , 1041 .
   Web of Science ®Google Scholar