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Chemistry. 2013 Mar 25;19(13):4135-9. doi: 10.1002/chem.201204148. Epub 2013 Feb 21.

Air-stable bifunctional allylation reagents for the asymmetric synthesis of differentiated syn- and anti-1,3-diols.

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  • 1Department of Chemistry, University of Texas at San Antonio, 1 UTSA Circle, San Antonio, TX 78249, USA.

Abstract

Turning the diols: Enantiomerically pure bifunctional reagents I and ent-I undergo asymmetric aldehyde allylation followed by Ir(I)-catalyzed enantioselective decarboxylative allylic etherification to give differentiated syn- and anti-1,3-diols with complete control of the absolute and relative stereochemistry (see scheme; PMP = para-methoxyphenyl, dbcot = dibenzo[a,e]cyclooctatetraene, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene).

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PMID:
23436704
[PubMed]
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