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Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids.
J Am Chem Soc. 2004 Aug 18; 126(32):9906-7.JA

Abstract

The development of readily accessible bifunctional chiral catalysts is a desirable yet challenging goal in catalytic asymmetric synthesis. In this communication, we describe the development of a new class of readily accessible chiral bifunctional organic catalysts that could be derived in one or two steps in high yield from either quinidine or quinine. These catalysts have been shown to catalyze a highly enantioselective conjugate addition of methyl and ethyl malonates and beta-ketoesters to a broad range of beta-substituted nitroalkenes, an synthetically important C-C bond-forming reaction utilizing readily available starting materials. This new catalytic asymmetric reaction proceeds in 91-98% ee and 71-99% yield.

Authors+Show Affiliations

Li H
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Wang Y
No affiliation info available
Tang L
No affiliation info available
Deng L
No affiliation info available

MeSH

AlkenesCatalysisCinchona AlkaloidsEstersKetonesMalonatesNitro CompoundsQuinidineStereoisomerism

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15303849

Citation

Li, Hongming, et al. "Highly Enantioselective Conjugate Addition of Malonate and Beta-ketoester to Nitroalkenes: Asymmetric C-C Bond Formation With New Bifunctional Organic Catalysts Based On Cinchona Alkaloids." Journal of the American Chemical Society, vol. 126, no. 32, 2004, pp. 9906-7.
Li H, Wang Y, Tang L, et al. Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids. J Am Chem Soc. 2004;126(32):9906-7.
Li, H., Wang, Y., Tang, L., & Deng, L. (2004). Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids. Journal of the American Chemical Society, 126(32), 9906-7.
Li H, et al. Highly Enantioselective Conjugate Addition of Malonate and Beta-ketoester to Nitroalkenes: Asymmetric C-C Bond Formation With New Bifunctional Organic Catalysts Based On Cinchona Alkaloids. J Am Chem Soc. 2004 Aug 18;126(32):9906-7. PubMed PMID: 15303849.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids. AU - Li,Hongming, AU - Wang,Yi, AU - Tang,Liang, AU - Deng,Li, PY - 2004/8/12/pubmed PY - 2004/10/20/medline PY - 2004/8/12/entrez SP - 9906 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 126 IS - 32 N2 - The development of readily accessible bifunctional chiral catalysts is a desirable yet challenging goal in catalytic asymmetric synthesis. In this communication, we describe the development of a new class of readily accessible chiral bifunctional organic catalysts that could be derived in one or two steps in high yield from either quinidine or quinine. These catalysts have been shown to catalyze a highly enantioselective conjugate addition of methyl and ethyl malonates and beta-ketoesters to a broad range of beta-substituted nitroalkenes, an synthetically important C-C bond-forming reaction utilizing readily available starting materials. This new catalytic asymmetric reaction proceeds in 91-98% ee and 71-99% yield. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15303849/Highly_enantioselective_conjugate_addition_of_malonate_and_beta_ketoester_to_nitroalkenes:_asymmetric_C_C_bond_formation_with_new_bifunctional_organic_catalysts_based_on_cinchona_alkaloids_ DB - PRIME DP - Unbound Medicine ER -