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A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent.
Chem Commun (Camb). 2013 May 18; 49(40):4561-3.CC

Abstract

A series of α-substituted nitroolefins were employed in organocatalytic asymmetric Michael reactions with aldehydes. γ-Nitro carbonyl products were achieved in good yields (up to 86%) with good stereoselectivities (up to 96% ee and 24 : 1 dr). Reduction of the nitro group followed by intramolecular reductive amination successfully afforded various novel optically active 2,4-disubstituted pyrrolidine compounds.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zheng B
School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, PR China.
Wang H
No affiliation info available
Han Y
No affiliation info available
Liu C
No affiliation info available
Peng Y
No affiliation info available

MeSH

AldehydesAlkenesMolecular StructureNitro CompoundsPyrrolidines

Pub Type(s)

Journal Article

Language

eng

PubMed ID

23563435

Citation

Zheng, Bo, et al. "A Novel Method to Access Chiral Nonnatural 2,4-disubstituted Pyrrolidines From Aldehydes and Nitroolefins Only With an Α-substituent." Chemical Communications (Cambridge, England), vol. 49, no. 40, 2013, pp. 4561-3.
Zheng B, Wang H, Han Y, et al. A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent. Chem Commun (Camb). 2013;49(40):4561-3.
Zheng, B., Wang, H., Han, Y., Liu, C., & Peng, Y. (2013). A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent. Chemical Communications (Cambridge, England), 49(40), 4561-3. https://doi.org/10.1039/c3cc40583d
Zheng B, et al. A Novel Method to Access Chiral Nonnatural 2,4-disubstituted Pyrrolidines From Aldehydes and Nitroolefins Only With an Α-substituent. Chem Commun (Camb). 2013 May 18;49(40):4561-3. PubMed PMID: 23563435.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent. AU - Zheng,Bo, AU - Wang,Hui, AU - Han,Yong, AU - Liu,Changlu, AU - Peng,Yungui, Y1 - 2013/04/08/ PY - 2013/4/9/entrez PY - 2013/4/9/pubmed PY - 2013/10/25/medline SP - 4561 EP - 3 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 49 IS - 40 N2 - A series of α-substituted nitroolefins were employed in organocatalytic asymmetric Michael reactions with aldehydes. γ-Nitro carbonyl products were achieved in good yields (up to 86%) with good stereoselectivities (up to 96% ee and 24 : 1 dr). Reduction of the nitro group followed by intramolecular reductive amination successfully afforded various novel optically active 2,4-disubstituted pyrrolidine compounds. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/23563435/A_novel_method_to_access_chiral_nonnatural_24_disubstituted_pyrrolidines_from_aldehydes_and_nitroolefins_only_with_an_��_substituent_ L2 - https://doi.org/10.1039/c3cc40583d DB - PRIME DP - Unbound Medicine ER -