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Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional beta-isocupreidine derivatives.
J Am Chem Soc. 2008 Sep 24; 130(38):12596-7.JA

Abstract

The aza-MBH reaction of imines 1 and beta-naphthyl acrylate 2 in the presence of C-6' modified beta-isocupreidine derivative 1c (0.1 equiv) and beta-naphthol 5 (0.1 equiv) afforded the corresponding (3S)-aza-MBH adducts 4 in high yield and excellent enantiomeric excess. These catalytic conditions allowed the aliphatic imines to be employed for the first time as electrophilic partners of the aza-MBH reaction. The coexistence of two H-bond donors with different acidic strengths was found to be crucial for the observed high enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Abermil N
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Masson G
No affiliation info available
Zhu J
No affiliation info available

MeSH

AcrylatesAza CompoundsCatalysisHydroxyquinolinesIminesNaphthalenesNaphtholsQuinuclidinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

18729367

Citation

Abermil, Nacim, et al. "Highly Enantioselective Aza Morita-Baylis-Hillman Reaction Catalyzed By Bifunctional Beta-isocupreidine Derivatives." Journal of the American Chemical Society, vol. 130, no. 38, 2008, pp. 12596-7.
Abermil N, Masson G, Zhu J. Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional beta-isocupreidine derivatives. J Am Chem Soc. 2008;130(38):12596-7.
Abermil, N., Masson, G., & Zhu, J. (2008). Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional beta-isocupreidine derivatives. Journal of the American Chemical Society, 130(38), 12596-7. https://doi.org/10.1021/ja805122j
Abermil N, Masson G, Zhu J. Highly Enantioselective Aza Morita-Baylis-Hillman Reaction Catalyzed By Bifunctional Beta-isocupreidine Derivatives. J Am Chem Soc. 2008 Sep 24;130(38):12596-7. PubMed PMID: 18729367.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional beta-isocupreidine derivatives. AU - Abermil,Nacim, AU - Masson,Géraldine, AU - Zhu,Jieping, Y1 - 2008/08/26/ PY - 2008/8/30/pubmed PY - 2008/12/17/medline PY - 2008/8/30/entrez SP - 12596 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 130 IS - 38 N2 - The aza-MBH reaction of imines 1 and beta-naphthyl acrylate 2 in the presence of C-6' modified beta-isocupreidine derivative 1c (0.1 equiv) and beta-naphthol 5 (0.1 equiv) afforded the corresponding (3S)-aza-MBH adducts 4 in high yield and excellent enantiomeric excess. These catalytic conditions allowed the aliphatic imines to be employed for the first time as electrophilic partners of the aza-MBH reaction. The coexistence of two H-bond donors with different acidic strengths was found to be crucial for the observed high enantioselectivity. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/18729367/Highly_enantioselective_aza_Morita_Baylis_Hillman_reaction_catalyzed_by_bifunctional_beta_isocupreidine_derivatives_ L2 - https://doi.org/10.1021/ja805122j DB - PRIME DP - Unbound Medicine ER -