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Org Lett

Title:		More than a protective group: synthesis and applications of a new chiral silane
Author(s):		Campagna M; Trzoss M; Bienz S;
Address:		"Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland"
Journal Title:		Org Lett
Year:		2007
Volume:		20070822
Issue:		19
Page Number:		3793 - 3796
DOI:		10.1021/ol071382h
ISSN/ISBN:		1523-7060 (Print) 1523-7052 (Linking)
Abstract:		"Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaldehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized"
Keywords:
Notes:		"PubMed-not-MEDLINECampagna, Maurizio Trzoss, Michael Bienz, Stefan eng 2007/08/24 Org Lett. 2007 Sep 13; 9(19):3793-6. doi: 10.1021/ol071382h. Epub 2007 Aug 22"