Journal
TETRAHEDRON LETTERS
Volume 56, Issue 14, Pages 1911-1914Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.02.116
Keywords
Organocatalysis; Cinchona alkaloids; Hypervalent iodine; Phase-transfer catalysis
Categories
Funding
- Austrian Science Funds (FWF) by a Lise-Meitner fellowship [M1602]
- European Union through the EFRE INTERREG IV ETC-AT-CZ programme [M00146]
- Austrian Science Fund (FWF) [M 1602] Funding Source: researchfish
- Austrian Science Fund (FWF) [M1602] Funding Source: Austrian Science Fund (FWF)
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This communication describes the first proof of concept for an asymmetric alpha-cyanation of beta-ketoesters using a hypervalent iodine-based electrophilic cyanide-transfer reagent. A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alkaloids allows obtaining the target products in good yields and with moderate enantioselectivities up to er = 76:24 under operationally simple conditions. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.orgilicenses/by/4.0/).
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