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Regio- and enantioselective palladium-catalyzed allylic alkylation of nitromethane with monosubstituted allyl substrates: synthesis of (R)-rolipram and (R)-baclofen.
J Org Chem. 2012 Oct 19; 77(20):8980-5.JO

Abstract

The Pd-catalyzed asymmetric allylic alkylation (AAA) reaction of nitromethane with monosubstituted allyl substrates was realized for the first time to provide corresponding products in high yields with excellent regio- and enantioselectivities. The protocol was applied to the enantioselective synthesis of (R)-baclofen and (R)-rolipram.

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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, People's Republic of China.
Ding CH
No affiliation info available
Li XH
No affiliation info available
Huang JQ
No affiliation info available
Hou XL
No affiliation info available
Dai LX
No affiliation info available
Wang PJ
No affiliation info available

MeSH

AlkylationAllyl CompoundsBaclofenCatalysisMethaneMolecular StructureNitroparaffinsOrganometallic CompoundsPalladiumRolipramStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22992268

Citation

Yang, Xiao-Fei, et al. "Regio- and Enantioselective Palladium-catalyzed Allylic Alkylation of Nitromethane With Monosubstituted Allyl Substrates: Synthesis of (R)-rolipram and (R)-baclofen." The Journal of Organic Chemistry, vol. 77, no. 20, 2012, pp. 8980-5.
Yang XF, Ding CH, Li XH, et al. Regio- and enantioselective palladium-catalyzed allylic alkylation of nitromethane with monosubstituted allyl substrates: synthesis of (R)-rolipram and (R)-baclofen. J Org Chem. 2012;77(20):8980-5.
Yang, X. F., Ding, C. H., Li, X. H., Huang, J. Q., Hou, X. L., Dai, L. X., & Wang, P. J. (2012). Regio- and enantioselective palladium-catalyzed allylic alkylation of nitromethane with monosubstituted allyl substrates: synthesis of (R)-rolipram and (R)-baclofen. The Journal of Organic Chemistry, 77(20), 8980-5. https://doi.org/10.1021/jo301506p
Yang XF, et al. Regio- and Enantioselective Palladium-catalyzed Allylic Alkylation of Nitromethane With Monosubstituted Allyl Substrates: Synthesis of (R)-rolipram and (R)-baclofen. J Org Chem. 2012 Oct 19;77(20):8980-5. PubMed PMID: 22992268.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regio- and enantioselective palladium-catalyzed allylic alkylation of nitromethane with monosubstituted allyl substrates: synthesis of (R)-rolipram and (R)-baclofen. AU - Yang,Xiao-Fei, AU - Ding,Chang-Hua, AU - Li,Xiao-Hui, AU - Huang,Jian-Qiang, AU - Hou,Xue-Long, AU - Dai,Li-Xin, AU - Wang,Pin-Jie, Y1 - 2012/10/01/ PY - 2012/9/21/entrez PY - 2012/9/21/pubmed PY - 2013/3/23/medline SP - 8980 EP - 5 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 20 N2 - The Pd-catalyzed asymmetric allylic alkylation (AAA) reaction of nitromethane with monosubstituted allyl substrates was realized for the first time to provide corresponding products in high yields with excellent regio- and enantioselectivities. The protocol was applied to the enantioselective synthesis of (R)-baclofen and (R)-rolipram. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22992268/Regio__and_enantioselective_palladium_catalyzed_allylic_alkylation_of_nitromethane_with_monosubstituted_allyl_substrates:_synthesis_of__R__rolipram_and__R__baclofen_ L2 - https://doi.org/10.1021/jo301506p DB - PRIME DP - Unbound Medicine ER -