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Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes.
J Org Chem. 2009 Nov 06; 74(21):8396-9.JO

Abstract

A chiral Lewis acid catalyst was prepared by mixing 2 equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et(2)AlCl. In the presence of a catalytic amount of [4j](2)Al(III)Cl complex (0.05 equiv), reaction between alpha-isocyanoacetamides (2) and aldehydes (3) afforded the corresponding 5-aminooxazoles (1) in good yields and enantioselectivities. Complex [4j](2)Al(III)Cl isolated as a white solid displayed similar reactivity as that prepared in situ.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yue T
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Wang MX
No affiliation info available
Wang DX
No affiliation info available
Masson G
No affiliation info available
Zhu J
No affiliation info available

MeSH

AldehydesAluminumCatalysisCyanidesMagnetic Resonance SpectroscopyOrganophosphatesSpectrometry, Mass, Electrospray IonizationSpectrophotometry, InfraredStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19788173

Citation

Yue, Tao, et al. "Catalytic Asymmetric Passerini-type Reaction: Chiral Aluminum-organophosphate-catalyzed Enantioselective Alpha-addition of Isocyanides to Aldehydes." The Journal of Organic Chemistry, vol. 74, no. 21, 2009, pp. 8396-9.
Yue T, Wang MX, Wang DX, et al. Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes. J Org Chem. 2009;74(21):8396-9.
Yue, T., Wang, M. X., Wang, D. X., Masson, G., & Zhu, J. (2009). Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes. The Journal of Organic Chemistry, 74(21), 8396-9. https://doi.org/10.1021/jo9017765
Yue T, et al. Catalytic Asymmetric Passerini-type Reaction: Chiral Aluminum-organophosphate-catalyzed Enantioselective Alpha-addition of Isocyanides to Aldehydes. J Org Chem. 2009 Nov 6;74(21):8396-9. PubMed PMID: 19788173.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes. AU - Yue,Tao, AU - Wang,Mei-Xiang, AU - Wang,De-Xian, AU - Masson,Géraldine, AU - Zhu,Jieping, PY - 2009/10/1/entrez PY - 2009/10/1/pubmed PY - 2010/1/13/medline SP - 8396 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 21 N2 - A chiral Lewis acid catalyst was prepared by mixing 2 equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et(2)AlCl. In the presence of a catalytic amount of [4j](2)Al(III)Cl complex (0.05 equiv), reaction between alpha-isocyanoacetamides (2) and aldehydes (3) afforded the corresponding 5-aminooxazoles (1) in good yields and enantioselectivities. Complex [4j](2)Al(III)Cl isolated as a white solid displayed similar reactivity as that prepared in situ. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19788173/Catalytic_asymmetric_Passerini_type_reaction:_chiral_aluminum_organophosphate_catalyzed_enantioselective_alpha_addition_of_isocyanides_to_aldehydes_ L2 - https://doi.org/10.1021/jo9017765 DB - PRIME DP - Unbound Medicine ER -