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One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes through a catalytic tandem reaction using an amino acid lithium salt.
J Org Chem. 2011 Apr 01; 76(7):2305-9.JO

Abstract

One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes was achieved by a catalytic tandem reaction using a primary amino acid lithium salt, O-tert-butyldiphenylsilyl l-tyrosine lithium salt, as a catalyst. Various aryl, alkenyl, and alkyl aldehydes were converted into γ-nitroaldehydes via in situ generation of nitroalkenes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yoshida M
Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan. myoshida@eng.hokudai.ac.jp
Kitamikado N
No affiliation info available
Ikehara H
No affiliation info available
Hara S
No affiliation info available

MeSH

AldehydesAlkanesAlkenesAmino AcidsCatalysisLithiumMolecular StructureNitro CompoundsSaltsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21388203

Citation

Yoshida, Masanori, et al. "One-pot Asymmetric Synthesis of Γ-nitroaldehydes From Aldehydes and Nitroalkanes Through a Catalytic Tandem Reaction Using an Amino Acid Lithium Salt." The Journal of Organic Chemistry, vol. 76, no. 7, 2011, pp. 2305-9.
Yoshida M, Kitamikado N, Ikehara H, et al. One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes through a catalytic tandem reaction using an amino acid lithium salt. J Org Chem. 2011;76(7):2305-9.
Yoshida, M., Kitamikado, N., Ikehara, H., & Hara, S. (2011). One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes through a catalytic tandem reaction using an amino acid lithium salt. The Journal of Organic Chemistry, 76(7), 2305-9. https://doi.org/10.1021/jo102570p
Yoshida M, et al. One-pot Asymmetric Synthesis of Γ-nitroaldehydes From Aldehydes and Nitroalkanes Through a Catalytic Tandem Reaction Using an Amino Acid Lithium Salt. J Org Chem. 2011 Apr 1;76(7):2305-9. PubMed PMID: 21388203.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes through a catalytic tandem reaction using an amino acid lithium salt. AU - Yoshida,Masanori, AU - Kitamikado,Naoki, AU - Ikehara,Hiroto, AU - Hara,Shoji, Y1 - 2011/03/09/ PY - 2011/3/11/entrez PY - 2011/3/11/pubmed PY - 2011/9/29/medline SP - 2305 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 7 N2 - One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes was achieved by a catalytic tandem reaction using a primary amino acid lithium salt, O-tert-butyldiphenylsilyl l-tyrosine lithium salt, as a catalyst. Various aryl, alkenyl, and alkyl aldehydes were converted into γ-nitroaldehydes via in situ generation of nitroalkenes. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21388203/One_pot_asymmetric_synthesis_of_γ_nitroaldehydes_from_aldehydes_and_nitroalkanes_through_a_catalytic_tandem_reaction_using_an_amino_acid_lithium_salt_ L2 - https://doi.org/10.1021/jo102570p DB - PRIME DP - Unbound Medicine ER -