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Truly Catalytic and Chemoselective Cleavage of Benzylidene Acetal with Phosphomolybdic Acid Supported on Silica Gel
Author(s) -
Kumar Ponminor Senthil,
Kumar Gaddale Devanna Kishore,
Baskaran Sundarababu
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800963
Subject(s) - phosphomolybdic acid , chemistry , acetal , catalysis , cleavage (geology) , ether , silica gel , organic chemistry , ether cleavage , chemoselectivity , geotechnical engineering , fracture (geology) , engineering
Phosphomolybdic acid supported on silica gel provides a truly catalytic method for the chemoselective cleavage of benzylidene acetals having sensitive functional groups under mild conditions. It is easy to perform on large scale owing to minimal catalyst loading (0.5 mol‐%). Several sensitive functional groups such as TBDPS ether, ‐OMs, ‐OAc, allyl ether, N ‐Boc, N ‐Fmoc and N ‐Cbz are stable under the reaction conditions. In addition, benzylidene acetal is selectively cleaved in the presence of isopropylidene ketal.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)