Journal
TETRAHEDRON LETTERS
Volume 50, Issue 22, Pages 2628-2631Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.03.057
Keywords
Organocatalysis; Asymmetric synthesis; Oxygenations; Diazo compounds; Rearrangements
Categories
Funding
- NSFC [20602008, 20832005]
- Chinese Academy of Sciences [KSCX2-YW-R-23]
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Asymmetric synthesis of 3-hydroxyl-2-alkanones is achieved via one-pot, tandem organocatalytic aminoxylation of aldehydes and chemoselective CH2N2-induced homologation. Accelerating effect of water is observed in alpha-aminoxylation. MgCl2, a Lewis acid additive, improves the chemoselectivity of the diazomethane homologation to 6:1 in favor of ketone. (C) 2009 Elsevier Ltd. All rights reserved.
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