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Org Lett

Title:		"Iterative approach to enantiopure syn/anti-1,3-polyols via proline-catalyzed sequential alpha-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehydes"
Author(s):		Kondekar NB; Kumar P;
Address:		"Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India"
Journal Title:		Org Lett
Year:		2009
Volume:		11
Issue:		12
Page Number:		2611 - 2614
DOI:		10.1021/ol900868v
ISSN/ISBN:		1523-7052 (Electronic) 1523-7052 (Linking)
Abstract:		"Iterative use of proline-catalyzed tandem alpha-aminoxylation and HWE olefination of aldehydes provided a simple access to 1,3-polyols. The feasibility of this approach is initially studied to synthesize syn- and anti-1,3-diols and is further extended to a syn/syn-1,3,5-triol at a useful level of asymmetric induction and yield. Its usage is illustrated by the short synthesis of a hydroxylactone pheromone component, (2S,3S)-2-hydroxyhexylcyclopentanone"
Keywords:		Aldehydes/*chemistry Alkenes/chemistry Catalysis Molecular Structure Polymers/*chemical synthesis/chemistry Proline/*chemistry Stereoisomerism;
Notes:		"MedlineKondekar, Nagendra B Kumar, Pradeep eng Research Support, Non-U.S. Gov't 2009/05/20 Org Lett. 2009 Jun 18; 11(12):2611-4. doi: 10.1021/ol900868v"