An Efficient Method for the Chemoselective Preparation of Benzoylated 1,2-Diols from Epoxides

Abstract

A very efficient and highly regioselective ring-opening reaction of epoxides with benzoic acid and its derivatives in the presence of cat. amount of tetrabutylammonium bromide (TBAB) in anhydrous acetonitrile has been developed. This effective method is useful for the preparation of selectively protected diols as precursor for many organic syntheses such as those of acyclic nucleosides and other synthetic purposes. The advantages of this method are efficiency, selectivity, low cost, and the applicability in large-scale synthesis of b-benzoyloxyalkanols.

benzoylated 1,2-diol - benzoic acid - epoxides - aceto­nitrile - TBAB

References

1 Wilkinson SG. In Comprehensive Organic Chemistry   Vol. 1:  Stoddart JF. Pergamon Press; Oxford: 1979.  Chap 4.1. p.579-706  

2 Green TW. Wuts PGM. In Protective Groups in Organic Synthesis   3rd ed.:  John Wiley & Sons; New York: 1999. 

3 Larock RC. In Comprehensive Organic Transformation   VCH publishers; New York: 1989. 

4 Pearson AJ. Roush WR. In Handbook of Reagent for Organic Synthesis, Activating Agents and Protecting Groups   John Wiley & Sons; Chichester: 1999. 

5a Iranpoor N. Salehi P. Synthesis  1994,  1152 

5b Chini M. Crotti P. Macchia F. Synlett  1992,  673 

5c Mall T. Stamm H. J. Org. Chem.  1987,  52:  4812 

5d Smith AB. Liverton NJ. Hrib NJ. Sivaramakrishnan H. Wizenberg K. J. Am. Chem. Soc.  1986,  108:  3040 

5e Olah GA. Fung AP. Meidar D. Synthesis  1981,  280 

5f Posner GH. Rogers DZ. J. Am. Chem. Soc.  1977,  99:  8208 

5g Posner GH. Rogers DZ. J. Am. Chem. Soc.  1977,  99:  8214 

5h Posner GH. Rogers DZ. Kinzig CM. Gurria GM. Tetrahedron Lett.  1975,  3597 

5i Posner GH. Angew. Chem., Int. Ed. Engl.  1978,  17:  487 

5j Ellestad GA. Whaley HA. Patterson EL. J. Am. Chem. Soc.  1966,  88:  4110 

6a Parker RE. Isaacs NS. Chem. Rev.  1959,  59:  737 

6b Paknikar SK. Kirtane JG. Tetrahedron  1983,  39:  2323 

6c Bonini C. Righi G. Synthesis  1994,  225 

6d Smith JG. Synthesis  1984,  629 

6e Kotsuki H. Teraguchi M. Shimamoto N. Ochi M. Tetrahedron Lett.  1996,  37:  3727 

7a Iranpoor N. Tarrian T. Movahedi Z. Synthesis  1996,  1473 

7b Iranpoor N. Shakarrize M. Shiriny F. Synth. Commun.  1998,  28:  347 

7c Carron M. Sharpless KB. J. Org. Chem.  1985,  50:  1560 

8 Jacobsen EN. Kakiuchi F. Kensler RJ. Larrow J. Tokunaga M. Tetrahedron Lett.  1997,  38:  773 

9 Gurgiolo AE. Chem. Abstr.  1978,  38:  111225P 

10 Apparo S. Schmidt RR. Synthesis  1987,  896 

11 Iranpoor N. Firouzabadi H. Safavi A. Shekarriz M. Synth. Commun.  2002,  32:  2287 

12a Cohen T. Dughi M. Nataro VA. Pinkus G. J. Org. Chem.  1962,  27:  814 

12b Hirano M. Morimoto T. J. Chem. Soc., Perkin Trans. 2  1984,  1033 

13 Khalafi-Nezhad A. Soltani Rad MN. Hakimelahi GH. Design and Synthesis of Some Novel Acyclovir Analogs, Cyclohexan Acyclic Nucleosides   The Preceding of 10th Iranian Seminar of Organic Chemistry (ISOC10); Guilan University Iran: 2002, 10-20 September. 

14 Albanese D. Landini D. Penso M. Synthesis  1994,  34 

15 Santry LJ. Azer S. McClelland RA. J. Am. Chem. Soc.  1988,  110:  2909 

16 McClelland RA. Seaman NE. Cramm D. J. Am. Chem. Soc.  1984,  106:  4511 

17 Reginato G. Ricci A. Roelens S. Scapecchi S. J. Org. Chem.  1990,  55:  5132 

18 Vogel AI. Practical Organic Chemistry   Longmans, Grean and Co.; London England: 1954.  Chap. II. p.161-176  

19a Ricci A. Roelens S. Vannucchi A. J. Chem. Soc., Chem. Commun.  1985,  1457 

19b Kim S. Chang H. Kim WJ. J. Org. Chem.  1985,  50:  1751 

19c Pautard AM. Evans SA. J. Org. Chem.  1988,  53:  2300 

19d Iwasaki F. Maki T. Onomuura O. Nakashima W. Matsumura Y. J. Org. Chem.  2000,  65:  996