Mild and efficient deprotection of acetal-type protecting groups of hydroxyl functions by triethylsilyl triflate2,4,6-collidine combination

Heterocycles

Volumn 77, Issue 2, 2009, Pages 1089-1103

  Fujioka, Hiromichi ^a   Kubo, Ozora ^a   Okamoto, Kazuhisa ^a   Senami, Kento ^a   Okitsu, Takashi ^a   Ohnaka, Takuya ^a   Sawama, Yoshinari ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Acetal Type Protecting Group of Hydroxyl Function; Acid Labile Functional Group; Chemoselective; Deprotection; Weakly Basic Condition

Indexed keywords

EID: 70249148782     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)88     Document Type: Article

References (13)

1. T.W. Green, and P.G. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 John Wiley and Sons New York 297
2. J.R. Hanson Protecting Groups in Organic Synthesis 1st ed. 1999 Blackwell Science, Inc. Malden, MA 37
3. H. Fujioka, T. Okitsu, T. Ohnaka, Y. Sawama, O. Kubo, K. Okamoto, and Y. Kita Adv. Synth. Catal. 349 2007 636
4. For alkyl- and arylation of oxacyclic ethers by TESOTf-2,4,6-collidine- Gilman reagent combination, see: H. Fujioka, T. Ohnaka, T. Okitsu, K. Okamoto, Y. Sawama, and Y. Kita Heterocycles 72 2007 529
5. For deprotection of acetal group by TESOTf-2,4,6-collidine combination, see: H. Fujioka, T. Okitsu, Y. Sawama, N. Murata, R. Li, and Y. Kita J. Am. Chem. Soc. 128 2006 5930
6. Experiments on THP-ethers were reported in ref. 2.
7. Compounds 6a-d were diastereomeric mixtures.
8. M. Miyashita, A. Yoshikoshi, and P.A. Grieco J Org. Chem. 42 1977 3772
9. A.N. French, J. Cole, and T. Wirth Synlett 13 2004 2291
10. Y.S. Hon, C.F. Lee, R.J. Chen, and P.H. Szu Tetrahedron 57 2001 5991
11. R. Baati, A. Valleix, C. Mioskowski, D.K. Barma, and J.R. Falck Org. Lett. 2 2000 485
12. B.S. Babu, and K.K. Balasubramanian Synlett 8 1999 1261
13. H. Fujioka, T. Okitsu, T. Ohnaka, R. Li, O. Kubo, K. Okamoto, Y. Sawama, and Y. Kita J. Org. Chem. 72 2007 7898