@article { ISI:000319647600012,
	title = {Orientation of the beta-hydroxyl group controls the diastereoselectivity during the hydride reduction and grignard reaction of inososes},
	journal = {Tetrahedron},
	volume = {69},
	number = {25},
	year = {2013},
	month = {JUN},
	pages = {5144-5151},
	publisher = {PERGAMON-ELSEVIER SCIENCE LTD},
	address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND},
	abstract = {<p>A comparison of the results of the Grignard reaction and the hydride reduction of the carbonyl group of epi- and scyllo-inososes reveals that the extent of diastereoselectivity of these reactions is decided by the orientation of the beta-hydroxyl group (or its derivative). Presence of an axial beta-hydroxyl group generally results in the formation of relatively larger amount of the axial alcohol as a result of the reduction of the carbonyl group. The possible reasons for the observed differences in diastereoselectivity between the reactions of these isomeric epi- and scyllo-inososes have been discussed. The sequence of reactions reported here provides convenient access to C-allcylated inositols, such as iso-laminitol and iso-mytilitol as well as 2-O-methyl epi-inositol, an epimer of the naturally occurring ononitol. (C) 2013 Elsevier Ltd. All rights reserved.</p>},
	keywords = {Cyclitol, diastereoselectivity, Grignard, Inositol, Nucleophile, reduction},
	issn = {0040-4020},
	doi = {10.1016/j.tet.2013.04.081},
	author = {Jagdhane, Rajendra C. and Patil, Madhuri T. and Krishnaswamy, Shobhana and Shashidhar, Mysore S.}
}
