Er(OTf)3 as a Mild Cleaving Agents for Acetals and Ketals

Renato Dalpozzo; Antonio De Nino; Loredana Maiuolo; Monica Nardi; Antonio Procopio; Antonio Tagarelli

doi:10.1055/s-2004-815941

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Synthesis 2004(4): 496-498
DOI: 10.1055/s-2004-815941

SHORTPAPER

Er(OTf)₃ as a Mild Cleaving Agents for Acetals and Ketals

Renato Dalpozzo^a, Antonio De Nino^a, Loredana Maiuolo^a, Monica Nardi^a, Antonio Procopio*^b, Antonio Tagarelli^a
^a Dipartimento di Chimica Università della Calabria, Ponte Bucci, 87030, Arcavacata di Rende (CS), Italy
^b Dipartimento Farmaco-Biologico, Università degli Studi della Magna Graecia, Complesso Ninì Barbieri, Roccelletta di Borgia (CZ), Italy.
Fax: +39(984)492055.; e-Mail: procopio@unicz.it.;

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Publication History

Received 17 December 2003
Publication Date:
03 February 2004 (online)

Abstract
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Abstract

Er(OTf)₃ is proposed as a very gentle Lewis acid catalyst in a chemoselective method for the cleavage of alkyl and cyclic acetals and ketals at room temperature in wet nitromethane is presented.

Key words

erbium(III) triflate - Lewis acid catalyst - acetals - ketals

References

1a Anastas PT. Warner JC. Green Chemistry: Theory and Practice Oxford Science Publications; Oxford: 1998.

Crossref Google Scholar
1b Collins TC. Green Chemistry: Frontiers in Chemical Synthesis and Processes Oxford University Press; Oxford: 1998.

Crossref Google Scholar
1c Tundo P. Anastas P. St Clair Black D. Breen J. Collins T. Memoli S. Miyamoto J. Polyakoff M. Tumas W. Pure Appl. Chem. 2000, 72: 1207

Crossref Google Scholar
2a Bartoli G. Cupone G. Dalpozzo R. De Nino A. Maiuolo L. Marcantoni E. Procopio A. Synlett 2001, 1897

Crossref Google Scholar
2b Bartoli G. Cupone G. Dalpozzo R. De Nino A. Maiuolo L. Procopio A. Sambri L. Tagarelli A. Tetrahedron Lett. 2002, 43: 5945

Crossref Google Scholar
2c Dalpozzo R. De Nino A. Maiuolo L. Procopio A. Tagarelli A. Sindona G. Bartoli G. J. Org. Chem. 2002, 67: 9093

Crossref Google Scholar
2d Dalpozzo R. De Nino A. Maiuolo L. Procopio A. Nardi M. Bartoli G. Romeo R. Tetrahedron Lett. 2003, 44: 5621

Crossref Google Scholar
3a Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd Ed.: John Wiley and Sons; New York: 1999.

Google Scholar
3b Kocienski PJ. Protecting Groups 1st Ed.: Georg Thieme Verlag; Stuttgart: 1994.

Google Scholar
4a Steel PG. J. Chem. Soc., Perkin Trans. 1 2001, 2727

Crossref PubMed Google Scholar
4b Kobayashi S. Manabe K. Acc. Chem. Res. 2002, 35: 209

Crossref PubMed Google Scholar
4c Kobayashi S. Sugiura M. Kitagawa H. Lam WW.-L. Chem Rev. 2002, 102: 2227

Crossref PubMed Google Scholar
5a Marcantoni E. Nobili F. Bartoli G. Bosco M. Sambri L. J. Org. Chem. 1997, 62: 4183

Crossref Google Scholar
5b Carrigan MD. Sarapa D. Smith RC. Wieland LC. Mohan RS. J. Org. Chem. 2002, 67: 1027

Crossref Google Scholar
6 Kobayashi S. Nagayama S. Busujima T. J. Am. Chem. Soc. 1998, 120: 8287

Crossref Google Scholar
7 Tsuruta H. Yamaguchi K. Imamoto T. Chem. Commun. 1999, 1703

Crossref Google Scholar
8 Castell P. Galia M. Serra A. Salla JM. Ramis X. Polymer 2000, 41: 8465

Crossref Google Scholar

9

All the chemicals were purchased from commercial sources besides the protected ketals 16-19 in Table [2] , which were synthesized according the trivial literature methods. [2c]

10

Er(OTf)₃ can be purchased from Aldrich e41.00 for 5g (0.008 mol) meanwhile, the prices of Sc(OTf)₃ and Yb(OTf)₃ sold by Aldrich are e206.4 for 5 g (0.01 mol) and e79 for 5 g (0.008 mol), respectively.