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β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group.
Org Lett. 2015 Dec 18; 17(24):5966-9.OL

Abstract

The Pd(II)-catalyzed arylation of unactivated β-C(sp(3))-H bonds in α-hydroxy aliphatic acid with a variety of aryl iodides was developed utilizing an amino acid auxiliary as a directing group. This protocol provides access to biologically active β-arylated-α-hydroxy acid derivatives.

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Authors+Show Affiliations

Toba T
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Hu Y
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Tran AT
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Yu JQ
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

MeSH

Amino AcidsCatalysisHydrocarbons, IodinatedHydroxy AcidsMagnetic Resonance SpectroscopyMolecular StructurePalladium

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26635188

Citation

Toba, Tetsuya, et al. "Β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group." Organic Letters, vol. 17, no. 24, 2015, pp. 5966-9.
Toba T, Hu Y, Tran AT, et al. Β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group. Org Lett. 2015;17(24):5966-9.
Toba, T., Hu, Y., Tran, A. T., & Yu, J. Q. (2015). Β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group. Organic Letters, 17(24), 5966-9. https://doi.org/10.1021/acs.orglett.5b02900
Toba T, et al. Β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group. Org Lett. 2015 Dec 18;17(24):5966-9. PubMed PMID: 26635188.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group. AU - Toba,Tetsuya, AU - Hu,Yi, AU - Tran,Anh T, AU - Yu,Jin-Quan, Y1 - 2015/12/04/ PY - 2015/12/5/entrez PY - 2015/12/5/pubmed PY - 2016/4/30/medline SP - 5966 EP - 9 JF - Organic letters JO - Org Lett VL - 17 IS - 24 N2 - The Pd(II)-catalyzed arylation of unactivated β-C(sp(3))-H bonds in α-hydroxy aliphatic acid with a variety of aryl iodides was developed utilizing an amino acid auxiliary as a directing group. This protocol provides access to biologically active β-arylated-α-hydroxy acid derivatives. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26635188/β_C_sp_3___H_Arylation_of_α_Hydroxy_Acid_Derivatives_Utilizing_Amino_Acid_as_a_Directing_Group_ DB - PRIME DP - Unbound Medicine ER -