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Palladium-catalyzed regio-, diastereo-, and enantioselective allylation of nitroalkanes with monosubstituted allylic substrates.
J Org Chem. 2013 Jul 05; 78(13):6503-9.JO

Abstract

Pd-catalyzed asymmetric allylic alkylation of nitroalkanes and monosubstituted allylic substrates was performed to afford products with two adjacent chiral centers and with excellent regio-, diastereo-, and enantioselectivities. The usefulness of the protocol in organic synthesis was demonstrated by transformation of the product to an optically active homoallylamine, a 2,3-disubstituted tetrahydropyridine, and an α,β-disubstituted amino acid derivative.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang XF
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Yu WH
No affiliation info available
Ding CH
No affiliation info available
Ding QP
No affiliation info available
Wan SL
No affiliation info available
Hou XL
No affiliation info available
Dai LX
No affiliation info available
Wang PJ
No affiliation info available

MeSH

AlkanesAllyl CompoundsAllylamineAmino AcidsCatalysisMolecular StructureNitro CompoundsOrganometallic CompoundsPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23741970

Citation

Yang, Xiao-Fei, et al. "Palladium-catalyzed Regio-, Diastereo-, and Enantioselective Allylation of Nitroalkanes With Monosubstituted Allylic Substrates." The Journal of Organic Chemistry, vol. 78, no. 13, 2013, pp. 6503-9.
Yang XF, Yu WH, Ding CH, et al. Palladium-catalyzed regio-, diastereo-, and enantioselective allylation of nitroalkanes with monosubstituted allylic substrates. J Org Chem. 2013;78(13):6503-9.
Yang, X. F., Yu, W. H., Ding, C. H., Ding, Q. P., Wan, S. L., Hou, X. L., Dai, L. X., & Wang, P. J. (2013). Palladium-catalyzed regio-, diastereo-, and enantioselective allylation of nitroalkanes with monosubstituted allylic substrates. The Journal of Organic Chemistry, 78(13), 6503-9. https://doi.org/10.1021/jo400663d
Yang XF, et al. Palladium-catalyzed Regio-, Diastereo-, and Enantioselective Allylation of Nitroalkanes With Monosubstituted Allylic Substrates. J Org Chem. 2013 Jul 5;78(13):6503-9. PubMed PMID: 23741970.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed regio-, diastereo-, and enantioselective allylation of nitroalkanes with monosubstituted allylic substrates. AU - Yang,Xiao-Fei, AU - Yu,Wei-Hua, AU - Ding,Chang-Hua, AU - Ding,Qiu-Ping, AU - Wan,Shi-Li, AU - Hou,Xue-Long, AU - Dai,Li-Xin, AU - Wang,Pin-Jie, Y1 - 2013/06/24/ PY - 2013/6/8/entrez PY - 2013/6/8/pubmed PY - 2014/1/29/medline SP - 6503 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 13 N2 - Pd-catalyzed asymmetric allylic alkylation of nitroalkanes and monosubstituted allylic substrates was performed to afford products with two adjacent chiral centers and with excellent regio-, diastereo-, and enantioselectivities. The usefulness of the protocol in organic synthesis was demonstrated by transformation of the product to an optically active homoallylamine, a 2,3-disubstituted tetrahydropyridine, and an α,β-disubstituted amino acid derivative. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23741970/Palladium_catalyzed_regio__diastereo__and_enantioselective_allylation_of_nitroalkanes_with_monosubstituted_allylic_substrates_ L2 - https://doi.org/10.1021/jo400663d DB - PRIME DP - Unbound Medicine ER -