@article { ISI:000264206200011,
	title = {Regioselective O-acylation of myo-inositol 1,3,5-orthoesters: dependence of regioselectivity on the stoichiometry of the base},
	journal = {Tetrahedron},
	volume = {65},
	number = {13},
	year = {2009},
	month = {MAR},
	pages = {2703-2710},
	publisher = {PERGAMON-ELSEVIER SCIENCE LTD},
	address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND},
	abstract = {<p>A metal mediated unusual 1-3 acyl migration from C4-O to C2-OH of myo-inositol 1,3,5-orthoformate was observed during the alkylation of racemic 4-O-benzoyl-myo-inositol 1,3,5-orthoformate. This has been exploited for the selective esterification of either the C4(6)-OH or the C2-OH of myo-inositol by varying the amount of the base used. While the use of 1 equiv of the base (sodium hydride or potassium tert-butoxide) for the acylation of myo-inositol orthoesters gives the corresponding C4-ester exclusively, the use of two or more equivalents of base for the same reaction gives the C2-ester exclusively. The relatively higher stability of the alkoxide of racemic 2-O-acyl-myo-inositol 1,3,5-orthoester as compared to the alkoxide of 4-O-acyl-myo-inositol 1,3,5-orthoester is suggested to be responsible for the observed isomerization. (c) 2009 Elsevier Ltd. All rights reserved.</p>},
	keywords = {Acylation, Cyclitol, Inositol, Orthoester, Regioselectivity, transesterification},
	issn = {0040-4020},
	doi = {10.1016/j.tet.2009.01.060},
	author = {Sureshan, Kana M. and Devaraj, Subramanian and Shashidhar, Mysore S.}
}
