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Organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins.
Org Lett. 2013 May 17; 15(10):2358-61.OL

Abstract

The first organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral α-alkyl-α-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Qiao B
Institute of Chemical Biology and Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan, P. R. China, 475004, and Waksman Institute of Microbiology, Rutgers, the State University of New Jersey , Piscataway, New Jersey 08854, United States.
An Y
No affiliation info available
Liu Q
No affiliation info available
Yang W
No affiliation info available
Liu H
No affiliation info available
Shen J
No affiliation info available
Yan L
No affiliation info available
Jiang Z
No affiliation info available

MeSH

AlkenesCarboxylic AcidsCatalysisMolecular StructureNitro CompoundsOxazolesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23642091

Citation

Qiao, Baokun, et al. "Organocatalytic Asymmetric Michael Addition of 5H-oxazol-4-ones to Nitroolefins." Organic Letters, vol. 15, no. 10, 2013, pp. 2358-61.
Qiao B, An Y, Liu Q, et al. Organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins. Org Lett. 2013;15(10):2358-61.
Qiao, B., An, Y., Liu, Q., Yang, W., Liu, H., Shen, J., Yan, L., & Jiang, Z. (2013). Organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins. Organic Letters, 15(10), 2358-61. https://doi.org/10.1021/ol401062z
Qiao B, et al. Organocatalytic Asymmetric Michael Addition of 5H-oxazol-4-ones to Nitroolefins. Org Lett. 2013 May 17;15(10):2358-61. PubMed PMID: 23642091.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins. AU - Qiao,Baokun, AU - An,Yongqiang, AU - Liu,Qian, AU - Yang,Wenguo, AU - Liu,Hongjun, AU - Shen,Juan, AU - Yan,Lin, AU - Jiang,Zhiyong, Y1 - 2013/05/03/ PY - 2013/5/7/entrez PY - 2013/5/7/pubmed PY - 2014/6/3/medline SP - 2358 EP - 61 JF - Organic letters JO - Org Lett VL - 15 IS - 10 N2 - The first organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral α-alkyl-α-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23642091/Organocatalytic_asymmetric_Michael_addition_of_5H_oxazol_4_ones_to_nitroolefins_ L2 - https://doi.org/10.1021/ol401062z DB - PRIME DP - Unbound Medicine ER -