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Synthesis 2010(16): 2713-2720  
DOI: 10.1055/s-0029-1218849
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Mild and Chemoselective Synthesis and Deprotection of Geminal Diacetates Catalyzed by Titanium(IV) Halides

Misuk Junga, Jieun Yoona, Hak Sung Kimb, Jae-Sang Ryu*a
a Center for Cell Signaling and Drug Discovery Research, College of Pharmacy and Division of Life and Pharmaceutical Sciences, Ewha Womans University, 11-1 Daehyun-Dong, Seodaemun-Gu, Seoul 120-750, South Korea
Fax: +82(2)32772851; e-Mail: ryuj@ewha.ac.kr;
b College of Pharmacy, Wonkwang University, 344-2 Shinyong-Dong, Iksan, Jeonbuk 570-749, South Korea
Further Information

Publication History

Received 8 March 2010
Publication Date:
25 June 2010 (online)

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Abstract

A novel, mild, and chemoselective method was developed for the preparation of gem-diacetates from aldehydes and acetic anhydride in the presence of titanium(IV) fluoride (1-5 mol%) under solvent-free conditions at room temperature. The reaction showed a high chemoselectivity toward aldehydes in the presence of ketones. Moreover, titanium(IV) fluoride also catalyzed the deprotection of gem-diacetates to the corresponding aldehydes in water. This efficient and simple method has several benefits, including the use of an inexpensive catalyst, solvent-free conditions, mild reaction temperatures, and high yields, which make it both cost-effective­ and environmentally friendly.

Key words

aldehydes - protecting groups - chemoselectivity - deprotection - acylation

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