Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/102543
Title: Organocatalytic asymmetric Mannich reactions of 5H-oxazol-4-ones : highly enantio- and diastereoselective synthesis of chiral α-alkylisoserine derivatives
Authors: Han, Zhiqiang
Yang, Wenguo
Tan, Choon-Hong
Jiang, Zhiyong
Keywords: DRNTU::Science::Chemistry::Organic chemistry
Issue Date: 2013
Source: Han, Z., Yang, W., Tan, C. H., & Jiang, Z. (2013). Organocatalytic asymmetric Mannich reactions of 5H-oxazol-4-ones : highly enantio- and diastereoselective synthesis of chiral α-alkylisoserine derivatives. Advanced Synthesis & Catalysis, 355(8), 1505-1511.
Series/Report no.: Advanced synthesis & catalysis
Abstract: The first organocatalytic Mannich reaction of 5H-oxazol-4-ones with various readily prepared aryl- and alkylsulfonimides has been developed. Two commercially available pseudoenantiomeric Cinchona alkaloids-derived tertiary amine/ureas have been demonstrated as the most efficient catalysts to access the opposite enantiomers of the Mannich products with equally excellent enantio- and diastereoselectivities. From the Mannich adducts, important α-methyl-α-hydroxy-β-amino acid derivatives, such as the α-methylated C-13 side chain of taxol and taxotere, can be conveniently prepared.
URI: https://hdl.handle.net/10356/102543
http://hdl.handle.net/10220/19084
ISSN: 1615-4150
DOI: http://dx.doi.org/10.1002/adsc.201300135
Rights: © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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