Lithium hexafluorophosphate-catalyzed efficient tetrahydropyranylation of tertiary alcohols under mild reaction conditions

Synlett

Volumn , Issue 10, 2004, Pages 1802-1804

  Hamada, Nao ^a   Sato, Tsuneo ^a  

^a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

Alcohols; Lewis acids; Lithium hexafluorophosphate; Protecting groups; Tetrahydropyranylation

Indexed keywords

FLUOROPHOSPHATE; LITHIUM; PYRAN DERIVATIVE; TERT BUTYL ALCOHOL;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; MOLECULAR INTERACTION; MOLECULAR STABILITY; REACTION ANALYSIS; SYNTHESIS;

EID: 4143105737     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829550     Document Type: Article

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27. For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see: (a) Ref. 7 (b) Ref. 8a (c) Ref. 8c (d) Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S.; Patil, S. V. Monatsh. Chem. 2003, 134, 425. (e) Ref. 4 (f) Ref. 9b and references cited therein, (g) Ref. 10 (h) Palaniappan, S.; Ram, M. S.; Amarnath, C. A. Green Chem. 2002, 4, 369. (i) Gajare, A. S.; Sabde, D. P.; Shingare, M. S.; Wakharkar, R. D. Synth. Commun. 2002, 32, 1549. (J) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
28. For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see: (a) Ref. 7 (b) Ref. 8a (c) Ref. 8c (d) Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S.; Patil, S. V. Monatsh. Chem. 2003, 134, 425. (e) Ref. 4 (f) Ref. 9b and references cited therein, (g) Ref. 10 (h) Palaniappan, S.; Ram, M. S.; Amarnath, C. A. Green Chem. 2002, 4, 369. (i) Gajare, A. S.; Sabde, D. P.; Shingare, M. S.; Wakharkar, R. D. Synth. Commun. 2002, 32, 1549. (J) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
29. For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see: (a) Ref. 7 (b) Ref. 8a (c) Ref. 8c (d) Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S.; Patil, S. V. Monatsh. Chem. 2003, 134, 425. (e) Ref. 4 (f) Ref. 9b and references cited therein, (g) Ref. 10 (h) Palaniappan, S.; Ram, M. S.; Amarnath, C. A. Green Chem. 2002, 4, 369. (i) Gajare, A. S.; Sabde, D. P.; Shingare, M. S.; Wakharkar, R. D. Synth. Commun. 2002, 32, 1549. (J) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
30. For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see: (a) Ref. 7 (b) Ref. 8a (c) Ref. 8c (d) Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S.; Patil, S. V. Monatsh. Chem. 2003, 134, 425. (e) Ref. 4 (f) Ref. 9b and references cited therein, (g) Ref. 10 (h) Palaniappan, S.; Ram, M. S.; Amarnath, C. A. Green Chem. 2002, 4, 369. (i) Gajare, A. S.; Sabde, D. P.; Shingare, M. S.; Wakharkar, R. D. Synth. Commun. 2002, 32, 1549. (J) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
31. For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see: (a) Ref. 7 (b) Ref. 8a (c) Ref. 8c (d) Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S.; Patil, S. V. Monatsh. Chem. 2003, 134, 425. (e) Ref. 4 (f) Ref. 9b and references cited therein, (g) Ref. 10 (h) Palaniappan, S.; Ram, M. S.; Amarnath, C. A. Green Chem. 2002, 4, 369. (i) Gajare, A. S.; Sabde, D. P.; Shingare, M. S.; Wakharkar, R. D. Synth. Commun. 2002, 32, 1549. (J) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
32. For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see: (a) Ref. 7 (b) Ref. 8a (c) Ref. 8c (d) Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S.; Patil, S. V. Monatsh. Chem. 2003, 134, 425. (e) Ref. 4 (f) Ref. 9b and references cited therein, (g) Ref. 10 (h) Palaniappan, S.; Ram, M. S.; Amarnath, C. A. Green Chem. 2002, 4, 369. (i) Gajare, A. S.; Sabde, D. P.; Shingare, M. S.; Wakharkar, R. D. Synth. Commun. 2002, 32, 1549. (J) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
33. For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see: (a) Ref. 7 (b) Ref. 8a (c) Ref. 8c (d) Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S.; Patil, S. V. Monatsh. Chem. 2003, 134, 425. (e) Ref. 4 (f) Ref. 9b and references cited therein, (g) Ref. 10 (h) Palaniappan, S.; Ram, M. S.; Amarnath, C. A. Green Chem. 2002, 4, 369. (i) Gajare, A. S.; Sabde, D. P.; Shingare, M. S.; Wakharkar, R. D. Synth. Commun. 2002, 32, 1549. (J) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
34. For recent reports on other catalysts used to prepare tertiary alkyl THP ethers, see: (a) Ref. 7 (b) Ref. 8a (c) Ref. 8c (d) Bandgar, B. P.; Sadavarte, V. S.; Uppalla, L. S.; Patil, S. V. Monatsh. Chem. 2003, 134, 425. (e) Ref. 4 (f) Ref. 9b and references cited therein, (g) Ref. 10 (h) Palaniappan, S.; Ram, M. S.; Amarnath, C. A. Green Chem. 2002, 4, 369. (i) Gajare, A. S.; Sabde, D. P.; Shingare, M. S.; Wakharkar, R. D. Synth. Commun. 2002, 32, 1549. (J) Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.