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Rhodium-catalyzed asymmetric addition of arylboronic acids to beta-phthaliminoacrylate esters toward the synthesis of beta-amino acids.
J Am Chem Soc. 2010 Jan 20; 132(2):464-5.JA

Abstract

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to beta-phthaliminoacrylate esters took place efficiently to give high yields of beta-aryl-beta-amino acid esters with 96-99% enantioselectivity, which was realized by use of a hydroxorhodium/chiral diene complex.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Nishimura T
Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan. tnishi@kuchem.kyoto-u.ac.jp
Wang J
No affiliation info available
Nagaosa M
No affiliation info available
Okamoto K
No affiliation info available
Shintani R
No affiliation info available
Kwong FY
No affiliation info available
Yu WY
No affiliation info available
Chan AS
No affiliation info available
Hayashi T
No affiliation info available

MeSH

AcrylatesAmino AcidsBoronic AcidsCatalysisMolecular StructureOrganometallic CompoundsPhthalic AcidsRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20028118

Citation

Nishimura, Takahiro, et al. "Rhodium-catalyzed Asymmetric Addition of Arylboronic Acids to Beta-phthaliminoacrylate Esters Toward the Synthesis of Beta-amino Acids." Journal of the American Chemical Society, vol. 132, no. 2, 2010, pp. 464-5.
Nishimura T, Wang J, Nagaosa M, et al. Rhodium-catalyzed asymmetric addition of arylboronic acids to beta-phthaliminoacrylate esters toward the synthesis of beta-amino acids. J Am Chem Soc. 2010;132(2):464-5.
Nishimura, T., Wang, J., Nagaosa, M., Okamoto, K., Shintani, R., Kwong, F. Y., Yu, W. Y., Chan, A. S., & Hayashi, T. (2010). Rhodium-catalyzed asymmetric addition of arylboronic acids to beta-phthaliminoacrylate esters toward the synthesis of beta-amino acids. Journal of the American Chemical Society, 132(2), 464-5. https://doi.org/10.1021/ja909642h
Nishimura T, et al. Rhodium-catalyzed Asymmetric Addition of Arylboronic Acids to Beta-phthaliminoacrylate Esters Toward the Synthesis of Beta-amino Acids. J Am Chem Soc. 2010 Jan 20;132(2):464-5. PubMed PMID: 20028118.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed asymmetric addition of arylboronic acids to beta-phthaliminoacrylate esters toward the synthesis of beta-amino acids. AU - Nishimura,Takahiro, AU - Wang,Jun, AU - Nagaosa,Makoto, AU - Okamoto,Kazuhiro, AU - Shintani,Ryo, AU - Kwong,Fuk-yee, AU - Yu,Wing-yiu, AU - Chan,Albert S C, AU - Hayashi,Tamio, PY - 2009/12/24/entrez PY - 2009/12/24/pubmed PY - 2010/3/27/medline SP - 464 EP - 5 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 2 N2 - Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to beta-phthaliminoacrylate esters took place efficiently to give high yields of beta-aryl-beta-amino acid esters with 96-99% enantioselectivity, which was realized by use of a hydroxorhodium/chiral diene complex. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20028118/Rhodium_catalyzed_asymmetric_addition_of_arylboronic_acids_to_beta_phthaliminoacrylate_esters_toward_the_synthesis_of_beta_amino_acids_ L2 - https://doi.org/10.1021/ja909642h DB - PRIME DP - Unbound Medicine ER -