Sc(OTf)3, an Efficient Catalyst for Formation and Deprotection of Geminal Diacetates (Acylals); Chemoselective Protection of Aldehydes in Presence of Ketones

Varinder K. Aggarwal; Silvia Fonquerna; Graham P. Vennall

doi:10.1055/s-1998-1799

Synlett 1998; 1998(8): 849-850
DOI: 10.1055/s-1998-1799

letter

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Sc(OTf)₃, an Efficient Catalyst for Formation and Deprotection of Geminal Diacetates (Acylals); Chemoselective Protection of Aldehydes in Presence of Ketones

Varinder K. Aggarwal^* , Silvia Fonquerna, Graham P. Vennall

^*Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK

Abstract

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Scandium triflate (2 mol%) has been found to be an extremely efficient catalyst for the addition of acetic anhydride to both aromatic and aliphatic aldehydes. Deprotection of the resulting geminal diacetates (acylals) was achieved using the same catalyst in the presence of water.

acylal - Lewis acid - Sc(OTf)₃ - protection - chemoselective

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