A MILD AND FEASIBLE DEPROTECTION OF ALCOHOL TETRAHYDROPYRANYL OR METHOXYMETHYL ETHERS CATALYZED BY Sc(OTf)₃

REFERENCES

• Hachiya , I. and Kobayashi , S. J. 1993 . Org. Chem. , 58 : 6958
   Web of Science ®Google Scholar
• Kawada , A. , Mitamura , S. and Kobayashi , S. 1994 . Synlett , : 545
   Google Scholar
• Kobayashi , S. 1994 . Synlett , : 689
   Web of Science ®Google Scholar
• Kobayashi , S. , Ishitani , H. and Nagayama , S . 1995 . Synthesis , : 1195
   Google Scholar
• Ishihara , K. , Kubota , M. , Kurihara , H. and Yamamoto , H. J. 1995 . Am. Chem. Soc. , 117 : 4413
   Web of Science ®Google Scholar
• Ishihara , K. , Kubota , M. , Kurihara , H. and Yamamoto , H. J. 1996 . Org. Chem. , 61 : 4560
   PubMed Web of Science ®Google Scholar
• Tsuchimoto , T. , Hiyama , T. and Fukuzawa , S. 1996 . J. Chem. Soc., Chem. Commun. , : 2345
   Google Scholar
• Kobayashi , S. , Moriwaki , M. , Akiyama , R. , Suzuki , S. and Hachiya , I. 1996 . Tetrahedron Lett. , 37 : 7783
   Web of Science ®Google Scholar
• Kobayashi , S. and Nagayama , S. 1997 . J. Am. Chem. Soc. , 119 : 10049
   Web of Science ®Google Scholar
• Tsuchimoto , T. , Tobita , K. , Hiyama , T. and Fukuzawa , S. J. 1997 . Org. Chem. , 62 : 6997
   Web of Science ®Google Scholar
• Aggarwal , V. K. , Vennall , G. P. , Davey , P. N. and Newman , C. 1998 . Tetrahedron Lett. , 39 : 1997
   Web of Science ®Google Scholar
• Kajiro , H. , Mitamura , S. , Mori , A. and Hiyama , T. 1998 . Synlett , : 51
   Web of Science ®Google Scholar
• Akiyama , T. and Iwai , J. 1998 . Synlett , : 273
   Web of Science ®Google Scholar
• Kobayashi , S. and Eur , J. 1999 . Org. Chem. , : 15
   Google Scholar
• Kobayashi , S. , Sugita , K. and Oyamada , H. 1999 . Synlett , : 138
   Google Scholar
• Kotsuki , H. , Arimura , K. , Araki , T. and Shinohara , T. 1999 . Synlett , : 462
   Web of Science ®Google Scholar
• Orita , A. , Nagano , Y. , Nakazawa , K. and Otera , J. 2000 . Synlett , : 599
   Web of Science ®Google Scholar
• Ma , Y. and Qian , C. 2000 . Tetrahedron Lett. , 41 : 945
   Web of Science ®Google Scholar
• Oriyama , T. , Kobayashi , Y. and Noda , K. 1998 . Synlett , : 1047
   Web of Science ®Google Scholar
• Miyashita , M. , Yoshikoshi , A. and Grieco , P. A. 1977 . J. Org. Chem. , 42 : 3772 Typical deprotection procedures for THP ethers
   Web of Science ®Google Scholar
• Ogawa , Y. and Shibasaki , M. 1984 . Tetrahedron Lett. , 25 : 663
   Web of Science ®Google Scholar
• Kim , S. and Park , J. H. 1987 . Tetrahedron Lett. , 28 : 439
   Web of Science ®Google Scholar
• Wagner , A. , Heitz , M.-P. and Mioskowski , C. 1989 . J. Chem. Soc., Chem. Commun. , : 1619
   Google Scholar
• Nambiar , K. P. and Mitra , A. 1994 . Tetrahedron Lett. , 35 : 3033
   Web of Science ®Google Scholar
• Srikrishna , A. , Sattigeri , J. A. , Viswajanani , R. and Yelamaggad , C. V. 1995 . J. Org. Chem. , 60 : 2260
   Web of Science ®Google Scholar
• Maiti , G. and Roy , S. C. 1996 . J. Org. Chem. , 61 : 6038
   Web of Science ®Google Scholar
• Heravi , M. M. , Ajami , D. , Mojtahedi , M. M. and Ghassemzadeh , M. 1999 . Tetrahedron Lett. , 40 : 561
   Web of Science ®Google Scholar
• Hon , Y.-S. and Lee , C.-F. 1999 . Tetrahedron Lett. , 40 : 2389
   Web of Science ®Google Scholar
• Kieczykowski , G. R. and Schlessinger , R. H. 1978 . J. Am. Chem. Soc. , 100 : 1938 Typical deprotection procedures for MOM ethers
   Web of Science ®Google Scholar
• Woodward , R. B. 1981 . 48 co-workers . J. Am. Chem. Soc. , 103 : 3210
   Google Scholar
• Bremmer , M. L. , Khatri , N. A. and Weinreb , S. M. 1983 . J. Org. Chem. , 48 : 3661
   Web of Science ®Google Scholar
• Quindon , Y. , Morton , H. E. and Yoakim , C. 1983 . Tetrahedron Lett. , 24 : 3969
   Google Scholar
• Corey , E. J. , Hua , D. H. and Seitz , S. P. 1984 . Tetrahedron Lett. , 25 : 3
   Web of Science ®Google Scholar
• Hanessian , S. , Delorme , D. and Dufresne , Y. 1984 . Tetrahedron Lett. , 25 : 2515
   Web of Science ®Google Scholar
• Boeckman , R. K. Jr. and Potenza , J. C. 1985 . Tetrahedron Lett. , 26 : 1411
   Web of Science ®Google Scholar
• Seto , H. and Mander , L. N. 1992 . Synth. Commun. , 22 : 2823
   Web of Science ®Google Scholar
• A typical experimental procedure is as follows (Table 2, Run 2): To scandium trifluoromethanesulfonate (7.5 mg, 0.015 mmol) was added 1-tetrahydropyranyloxy-3-phenylpropane (66.8 mg, 0.30 mmol) in CH3CN (1.5 ml) and CH3OH (1.0 ml, 24.7 mmol) at room temperature under argon atmosphere. The resultant mixture was stirred for 1 h at room temperature and quenched with buffer (pH 7). The organic materials were extracted with Et2O and dried over anhydrous sodium sulfate. The solvent was evaporated and 3-phenylpropanol (40.7 mg, 98%) was isolated by thin-layer chromatography on silica gel (ether:hexane=1:2). The product gave satisfactory 1H NMR and IR spectra
   Google Scholar