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Diastereoselective and enantioselective capture of chiral zinc enolate using nitroolefins: a rapid access to chiral γ-nitro carbonyl compounds.
Org Biomol Chem. 2011 Sep 21; 9(18):6211-4.OB

Abstract

Highly diastereoselective and enantioselective catalytic capture of chiral zinc enolates using nitroolefins as electrophiles is described. The tandem products γ-nitro ketones were obtained in good yields with high diastereoselectivities and enantioselectivities. The γ-nitro ketones were readily hydrogenated to the optically enriched and diastereomerically pure chiral pyrrolidines with four contiguous stereocentres under mild conditions.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ni CY
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, Nanchong, P R China.
Kan SS
No affiliation info available
Liu QZ
No affiliation info available
Kang TR
No affiliation info available

MeSH

AlkenesModels, MolecularNitro CompoundsPyrrolidinesStereoisomerismZinc

Pub Type(s)

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

Language

eng

PubMed ID

21814692

Citation

Ni, Cheng-Yan, et al. "Diastereoselective and Enantioselective Capture of Chiral Zinc Enolate Using Nitroolefins: a Rapid Access to Chiral Γ-nitro Carbonyl Compounds." Organic & Biomolecular Chemistry, vol. 9, no. 18, 2011, pp. 6211-4.
Ni CY, Kan SS, Liu QZ, et al. Diastereoselective and enantioselective capture of chiral zinc enolate using nitroolefins: a rapid access to chiral γ-nitro carbonyl compounds. Org Biomol Chem. 2011;9(18):6211-4.
Ni, C. Y., Kan, S. S., Liu, Q. Z., & Kang, T. R. (2011). Diastereoselective and enantioselective capture of chiral zinc enolate using nitroolefins: a rapid access to chiral γ-nitro carbonyl compounds. Organic & Biomolecular Chemistry, 9(18), 6211-4. https://doi.org/10.1039/c1ob05903c
Ni CY, et al. Diastereoselective and Enantioselective Capture of Chiral Zinc Enolate Using Nitroolefins: a Rapid Access to Chiral Γ-nitro Carbonyl Compounds. Org Biomol Chem. 2011 Sep 21;9(18):6211-4. PubMed PMID: 21814692.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Diastereoselective and enantioselective capture of chiral zinc enolate using nitroolefins: a rapid access to chiral γ-nitro carbonyl compounds. AU - Ni,Cheng-Yan, AU - Kan,Sha-Sha, AU - Liu,Quan-Zhong, AU - Kang,Tai-Ran, Y1 - 2011/08/04/ PY - 2011/8/5/entrez PY - 2011/8/5/pubmed PY - 2011/12/17/medline SP - 6211 EP - 4 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 9 IS - 18 N2 - Highly diastereoselective and enantioselective catalytic capture of chiral zinc enolates using nitroolefins as electrophiles is described. The tandem products γ-nitro ketones were obtained in good yields with high diastereoselectivities and enantioselectivities. The γ-nitro ketones were readily hydrogenated to the optically enriched and diastereomerically pure chiral pyrrolidines with four contiguous stereocentres under mild conditions. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/21814692/Diastereoselective_and_enantioselective_capture_of_chiral_zinc_enolate_using_nitroolefins:_a_rapid_access_to_chiral_γ_nitro_carbonyl_compounds_ L2 - https://doi.org/10.1039/c1ob05903c DB - PRIME DP - Unbound Medicine ER -