Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 6
3,265
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Microwave-Accelerated Selective Acylation of (Hydroxyalkyl)phenols Using Acid Chlorides

, &
Pages 1092-1099 | Received 18 Aug 2008, Published online: 25 Feb 2009

REFERENCES

  • Wuts , P. G. M. ; Greene , T. W. Greene's Protective Groups in Organic Synthesis, , 4th ed. ; Wiley : New York , 2007 .
  • Höfle , G. ; Steglich , W. ; Vorbrüggen , H. 4-Dialkylaminopyridines as highly active acylation catalysts . Angew. Chem. Int. Ed. Engl. 1978 , 17 , 569 – 583 .
  • For example, see (a) Mukaiyama , T. ; Pai , F.-C. ; Onaka , M. ; Narasaka , K. A useful method for selective acylation of alcohols using 2,2′-bipyridyl-6-yl carboxylate and cesium fluoride . Chem. Lett. 1980 , 563 – 566 ; (b) Paradisi , M. P. ; Zecchini , G. P. ; Torrini , I. Selective acylations of aminophenols and hydroxyalkylphenols with 1-acetyl-v-triazolo[4,5-b]pyridine . Tetrahedron Lett. 1986 , 27 , 5029 – 5032 ; (c) Yamada , S. ; Sugaki , T. ; Matsuzaki , K. Twisted amides as selective acylating agents for hydroxyl groups under neutral conditions: Models for activated peptides during enzymatic acyl transfer reaction . J. Org. Chem. 1996 , 61 , 5932 – 5938 .
  • For example, see (a) Breton , G. W. Selective monoacylation of unsymmetrical diols catalyzed by silica gel-supported sodium hydrogen sulfate . J. Org. Chem. 1997 , 62 , 8952 – 8954 ; (b) Orita , A. ; Mitsutome , A. ; Otera , J. Distannoxane-catalyzed highly selective acylation of alcohols . J. Org. Chem. 1998 , 63 , 2420 – 2421 ; (c) Caddick , S. ; McCarroll , A. J. ; Sandham , D. A. A convenient and practical method for the selective benzoylation of primary hydroxyl groups using microwave heating . Tetrahedron 2001 , 57 , 6305 – 6310 ; (d) Clarke , P. A. Selective mono-acylation of meso- and C 2-symmetric 1,3- and 1,4-diols . Tetrahedron Lett. 2002 , 43 , 4761 – 4763 .
  • For reviews, see (a) Bornscheuer , U. T. ; Kazlauskas , R. J. Chemo- and regioselective lipase-catalyzed reactions . In Hydrolases in Organic Synthesis, , 2nd ed. ; Wiley-VHC : Weinheim , 2006 ; 141 ; (b) Faber , K. Biotransformations in Organic Chemistry, , 5th ed. ; Springer : Berlin , 2004 ; 363 .
  • Miyazawa , T. ; Hamada , M. ; Morimoto , R. ; Murashima , T. ; Yamada , T. Highly regioselective propanoylation of dihydroxybenzenes mediated by Candida antarctica lipase B in organic solvents . Tetrahedron Lett. 2008 , 49 , 175 – 178 .
  • Miyazawa , T. ; Hamada , M. ; Morimoto , R. ; Murashima , T. ; Yamada , T. Secondary alcohols act as better nucleophiles than primary alcohols in the lipase-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxyls . Tetrahedron Lett. 2007 , 48 , 8334 – 8337 .
  • For reviews, see (a) Microwaves in Organic Synthesis, , 2nd ed. ; A. Loupy , (Ed.); Wiley-VCH : Weinheim , 2006 ; (b) Microwaves in Organic and Medicinal Chemistry ; C. O. Kappe , and A. Stadler (Eds.); Wiley-VCH : Weinheim , 2005 .
  • de la Hoz , A. ; Díaz-Ortiz , A. ; Moreno , A. Selectivity under the action of microwave irradiation . In Microwaves in Organic Synthesis, , 2nd ed. ; A. Loupy and A. Stadler (Eds.); Wiley-VCH : Weinheim , 2005 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.