Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 17, Pages 2836-2844Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900226
Keywords
Allenes; Copper; Homogeneous catalysis; Nucleophilic substitution; Grignard reaction
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Funding
- European Union [MEST-CT-2005-019780]
- UK government, Engineering and Physical Sciences Research Council (EPSRC) [EP/F033478/1]
- EPSRC [EP/F033478/1, EP/G026882/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/F033478/1, EP/G026882/1] Funding Source: researchfish
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A new catalytic method for the synthesis of alpha-hydroxyallenes is described. Efficient S(N)2' substitution of propargylic dioxolanones has been achieved with a copper(I)/P(OBu)(3) catalyst using Grignard reagents as the nucleophiles. The reaction tolerates a wide variety of propargylic dioxolanones, the cor-responding primary and secondary alpha-hydroxyallenes are obtained in good to excellent yields and excellent diastereoseletivity. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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