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Enantioselective Michael reactions of beta, beta-disubstituted nitroalkenes: a new approach to beta(2,2)-amino acids with hetero-quaternary stereocenters.
Org Lett. 2009 Sep 03; 11(17):3946-9.OL

Abstract

An atom-economic organocatalytic asymmetric Michael reaction of alpha,beta,beta-trisubstituted olefins has been successfully developed. The reaction exhibits excellent enantioselectivities under low loading of catalysts, and the conjugate addition products are valuable for the synthesis of novel beta(2,2)-amino acids and beta-peptides.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Lu HH
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Zhang FG
No affiliation info available
Meng XG
No affiliation info available
Duan SW
No affiliation info available
Xiao WJ
No affiliation info available

MeSH

AlkenesAmino AcidsCatalysisCombinatorial Chemistry TechniquesMolecular StructureNitro CompoundsPeptidesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19653671

Citation

Lu, Hai-Hua, et al. "Enantioselective Michael Reactions of Beta, Beta-disubstituted Nitroalkenes: a New Approach to Beta(2,2)-amino Acids With Hetero-quaternary Stereocenters." Organic Letters, vol. 11, no. 17, 2009, pp. 3946-9.
Lu HH, Zhang FG, Meng XG, et al. Enantioselective Michael reactions of beta, beta-disubstituted nitroalkenes: a new approach to beta(2,2)-amino acids with hetero-quaternary stereocenters. Org Lett. 2009;11(17):3946-9.
Lu, H. H., Zhang, F. G., Meng, X. G., Duan, S. W., & Xiao, W. J. (2009). Enantioselective Michael reactions of beta, beta-disubstituted nitroalkenes: a new approach to beta(2,2)-amino acids with hetero-quaternary stereocenters. Organic Letters, 11(17), 3946-9. https://doi.org/10.1021/ol901572x
Lu HH, et al. Enantioselective Michael Reactions of Beta, Beta-disubstituted Nitroalkenes: a New Approach to Beta(2,2)-amino Acids With Hetero-quaternary Stereocenters. Org Lett. 2009 Sep 3;11(17):3946-9. PubMed PMID: 19653671.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Michael reactions of beta, beta-disubstituted nitroalkenes: a new approach to beta(2,2)-amino acids with hetero-quaternary stereocenters. AU - Lu,Hai-Hua, AU - Zhang,Fu-Gen, AU - Meng,Xiang-Gao, AU - Duan,Shu-Wen, AU - Xiao,Wen-Jing, PY - 2009/8/6/entrez PY - 2009/8/6/pubmed PY - 2009/9/24/medline SP - 3946 EP - 9 JF - Organic letters JO - Org Lett VL - 11 IS - 17 N2 - An atom-economic organocatalytic asymmetric Michael reaction of alpha,beta,beta-trisubstituted olefins has been successfully developed. The reaction exhibits excellent enantioselectivities under low loading of catalysts, and the conjugate addition products are valuable for the synthesis of novel beta(2,2)-amino acids and beta-peptides. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19653671/Enantioselective_Michael_reactions_of_beta_beta_disubstituted_nitroalkenes:_a_new_approach_to_beta_22__amino_acids_with_hetero_quaternary_stereocenters_ L2 - https://doi.org/10.1021/ol901572x DB - PRIME DP - Unbound Medicine ER -