Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 19, Pages 2683-2691Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601640
Keywords
Asymmetric synthesis; Fullerenes; Thioureas; Michael addition; Organocatalysis
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Funding
- Spanish MINECO [CTQ2014-59870-P]
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Three novel fullerothioureas derived from natural valine, phenylalanine, and tert-leucine have been prepared by Prato's reaction of [60]fullerene and the corresponding aldehydes. These hybrids have been used as organocatalysts in a typical stereoselective nitro-Michael addition reaction under homogeneous and neat conditions. The catalysts are easily recoverable by filtration, and are recyclable for at least five times. The addition products were obtained in excellent yields and stereoselectivities by using catalyst loadings of as low as 0.5 mol-%.
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