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Environment friendly chemoselective deprotection of acetonides and cleavage of acetals and ketals in aqueous medium without using any catalyst or organic solvent

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Abstract

Highly chemoselective environment friendly deprotection of acetonides and cleavage of acetals and ketones has been achieved by heating in aqueous medium without using any catalyst and organic solvent.

A chemoselective environment friendly methodology has been developed for deprotection of acetonides and cleavage of acetals and ketones in aqueous medium without using any catalyst and organic solvent.

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References

  1. (a) Schkeryantz J M and Danishefsky S J 1995 J. Am. Chem. Soc. 117 4722; (b) Masters J J, Link J T, Snyder L B, Young W B and Danishefsky S J 1995 Angew. Chem., Int. Ed. Engl. 34 1723; (c) Boyce R J and Pattenden G 1996 Tetrahedron Lett. 37 3501

  2. (a) Clode D M 1979 Chem. Rev. 79 491; (b) Nicolaou K C, Daines R A, Uenishi J, Li W S, Papahatjis D P and Chakraborty T K 1988 J. Am. Chem. Soc. 110 4672

  3. (a) Banerjee S and Ghosh S J 2003 Org. Chem. 68 3981; (b) Krishna P R, Kannan V and Sharma G V M 2004 J. Org. Chem. 69 6467; (c) Hanessian S, Huang G, Chenel C, Machaalani R and Loiseleur O 2005 J. Org. Chem. 70 6721; (d) Sharma G V M and Gopinath T 2005 Tetrahedron Lett. 46 1307

  4. (a) Fleet G W J and Smith P W 1985 Tetrahedron Lett. 26 1469; (b) Gerspacher M and Rapoport H 1991 J. Org. Chem. 56 3700; (c) Yadav J S, Chander M C and Reddy K K 1992 Tetrahedron Lett. 33 135; (d) Manna S, Viala J, Yadagiri P and Falck J R 1986 Tetrahedron Lett. 27 2679; (e) Park K H, Yoon Y J and Lee S G 1994 Tetrahedron Lett. 35 9737; (f) Leblanc Y, Fitzsimmons B J, Adams J, Perez F and Rokach J 1986 J. Org. Chem. 51 789; (g) Baurle S, Hoppen S and Koert U 1999 Angew. Chem., Int. Ed. 38 1263; (h) Ichihara A, Ubukata M and Sakamura S 1997 Tetrahedron Lett. 38 3473

  5. (a) Barbot F and Miginiac P 1983 Synthesis 651; (b) Sterzycki R 1979 Synthesis 724; (c) Kantam M L, Swapna V and Santhi P L 1995 Synth. Commun. 25 2529; (d) Xiao X and Bai D 2001 Synlett 4, 535; (e) Vijayasaradhi S, Singh J and Aidhen I S 2000 Synlett 1 110; (f) Kim K S, Song Y H, Lee B H and Hahn C S 1986 J. Org. Chem. 51 404; (g) Yadav J S, Raghavendra S, Satyanarayana M and Balanarsaiah E 2005 Synlett 16 2461; (h) Swamy N R and Venkateswarlu Y 2002 Tetrahedron Lett. 43 7549; (i) Chari M A and Syamasundar K 2005 Synthesis 708; (j) Reddy S M, Reddy Y V and Venkateswarlu Y 2005 Tetrahedron Lett. 46 7439; (k) Maddani M R and Prabhu K R 2011 Synlett 6 821; (l) Yadav J S, Satyanarayana M, Raghavendra S and Balanarsaiah E 2005 Tetrahedron Lett. 46 8745; (m) Fleet G W J and Witty D R 1990 Tetrahedron: Asymmetry 1 119; (n) Rajput V K, Roy B and Mukhopadhyay B 2006 Tetrahedron Lett. 47 6987; (o) Barrades J S, Errea M I and Accorso N B D 2012 Carbohyd. Res. 355 79; (p) Shing T K M and Leung G Y C 2002 Tetrahedron 58 7545; (q) Sharma G V M, Yadav T A, Choudhury M and Kunwar A C 2012 J. Org. Chem. 77 6834; (r) Christiane M and Carreira E M 2005 J. Am. Chem. Soc. 127 11505

  6. (a) Maiti G and Roy S C 1996 J. Org. Chem. 61 6038; (b) Mandal P K, Dutta P and Roy S C 1997 Tetrahedron Lett. 38 7271; (c) Jana S and Roy S C 2007 Indian J. Chem. 46B 707

  7. (a) Habibi M, Tangestaninejad S, Baltork I, Mirkhani V and Yadollahi B 2001 Tetrahedron Lett. 42 6771; (b) Li J, Wu Y, Fuller N, Markus M and Li W J 2010 Org. Chem. 75 1077; (c) Yuan C, Yang Li, Yue G, Yu T, Zhong W and Liu B 2012 Tetrahedron Lett. 53 6972

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Acknowledgements

We thank the Department of Science and Technology (DST), New Delhi for financial support (SR/S-1/OC-12/2011). SM thanks the Council of Scientific and Industrial Research (CSIR), New Delhi for the award of Fellowship.

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MUKHERJEE, S., SENGUPTA, A. & ROY, S.C. Environment friendly chemoselective deprotection of acetonides and cleavage of acetals and ketals in aqueous medium without using any catalyst or organic solvent. J Chem Sci 125, 1493–1496 (2013). https://doi.org/10.1007/s12039-013-0514-7

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  • DOI: https://doi.org/10.1007/s12039-013-0514-7

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