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Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst.
Org Biomol Chem. 2012 Apr 14; 10(14):2840-6.OB

Abstract

Perhydroindolic acids, the by-products obtained in the industrial production of a trandolapril intermediate, were used as chiral organocatalysts in asymmetric Michael addition reactions of aldehydes to nitroolefins. These proline-like catalysts are unique for their rigid bicyclic structure with two H atoms attached to the bridgehead C atoms lying on the opposite side of the ring. They therefore showed high efficiency in asymmetric Michael additions of aldehydes to nitroolefins. Under the optimal conditions, excellent diastereo- and enantioselectivities (up to 99/1 dr and 98% ee) were obtained with high chemical yields for a series of aldehydes and nitroolefins using only 5 mol% catalyst loading. The methodology features easily available catalysts, high catalytic efficiency and environmentally green procedures.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhao L
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, PR China.
Shen J
No affiliation info available
Liu D
No affiliation info available
Liu Y
No affiliation info available
Zhang W
No affiliation info available

MeSH

Acids, HeterocyclicAldehydesAlkenesCatalysisMolecular StructureNitrogen CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22388774

Citation

Zhao, Lina, et al. "Highly Efficient Asymmetric Michael Addition of Aldehyde to Nitroolefin Using Perhydroindolic Acid as a Chiral Organocatalyst." Organic & Biomolecular Chemistry, vol. 10, no. 14, 2012, pp. 2840-6.
Zhao L, Shen J, Liu D, et al. Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst. Org Biomol Chem. 2012;10(14):2840-6.
Zhao, L., Shen, J., Liu, D., Liu, Y., & Zhang, W. (2012). Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst. Organic & Biomolecular Chemistry, 10(14), 2840-6. https://doi.org/10.1039/c2ob00003b
Zhao L, et al. Highly Efficient Asymmetric Michael Addition of Aldehyde to Nitroolefin Using Perhydroindolic Acid as a Chiral Organocatalyst. Org Biomol Chem. 2012 Apr 14;10(14):2840-6. PubMed PMID: 22388774.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst. AU - Zhao,Lina, AU - Shen,Jiefeng, AU - Liu,Delong, AU - Liu,Yangang, AU - Zhang,Wanbin, Y1 - 2012/03/02/ PY - 2012/3/6/entrez PY - 2012/3/6/pubmed PY - 2012/8/1/medline SP - 2840 EP - 6 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 14 N2 - Perhydroindolic acids, the by-products obtained in the industrial production of a trandolapril intermediate, were used as chiral organocatalysts in asymmetric Michael addition reactions of aldehydes to nitroolefins. These proline-like catalysts are unique for their rigid bicyclic structure with two H atoms attached to the bridgehead C atoms lying on the opposite side of the ring. They therefore showed high efficiency in asymmetric Michael additions of aldehydes to nitroolefins. Under the optimal conditions, excellent diastereo- and enantioselectivities (up to 99/1 dr and 98% ee) were obtained with high chemical yields for a series of aldehydes and nitroolefins using only 5 mol% catalyst loading. The methodology features easily available catalysts, high catalytic efficiency and environmentally green procedures. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22388774/Highly_efficient_asymmetric_Michael_addition_of_aldehyde_to_nitroolefin_using_perhydroindolic_acid_as_a_chiral_organocatalyst_ L2 - https://doi.org/10.1039/c2ob00003b DB - PRIME DP - Unbound Medicine ER -