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Synthesis of optically active β- or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents.
J Org Chem. 2013 Sep 06; 78(17):8274-80.JO

Abstract

An efficient one-pot synthesis of optically active β-alkyl-substituted alcohols through a tandem copper-catalyzed asymmetric allylic alkylation (AAA) with organolithium reagents and reductive ozonolysis is presented. Furthermore, hydroboration-oxidation following the Cu-catalyzed AAA leads to the corresponding homochiral γ-alkyl-substituted alcohols.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Guduguntla S
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Fañanás-Mastral M
No affiliation info available
Feringa BL
No affiliation info available

MeSH

AlcoholsAlkylationAllyl CompoundsCatalysisCopperLithiumMolecular StructureOptical PhenomenaOrganometallic Compounds

Pub Type(s)

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

Language

eng

PubMed ID

23962149

Citation

Guduguntla, Sureshbabu, et al. "Synthesis of Optically Active Β- or Γ-alkyl-substituted Alcohols Through Copper-catalyzed Asymmetric Allylic Alkylation With Organolithium Reagents." The Journal of Organic Chemistry, vol. 78, no. 17, 2013, pp. 8274-80.
Guduguntla S, Fañanás-Mastral M, Feringa BL. Synthesis of optically active β- or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents. J Org Chem. 2013;78(17):8274-80.
Guduguntla, S., Fañanás-Mastral, M., & Feringa, B. L. (2013). Synthesis of optically active β- or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents. The Journal of Organic Chemistry, 78(17), 8274-80. https://doi.org/10.1021/jo401536u
Guduguntla S, Fañanás-Mastral M, Feringa BL. Synthesis of Optically Active Β- or Γ-alkyl-substituted Alcohols Through Copper-catalyzed Asymmetric Allylic Alkylation With Organolithium Reagents. J Org Chem. 2013 Sep 6;78(17):8274-80. PubMed PMID: 23962149.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of optically active β- or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents. AU - Guduguntla,Sureshbabu, AU - Fañanás-Mastral,Martín, AU - Feringa,Ben L, Y1 - 2013/08/23/ PY - 2013/8/22/entrez PY - 2013/8/22/pubmed PY - 2013/12/16/medline SP - 8274 EP - 80 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 17 N2 - An efficient one-pot synthesis of optically active β-alkyl-substituted alcohols through a tandem copper-catalyzed asymmetric allylic alkylation (AAA) with organolithium reagents and reductive ozonolysis is presented. Furthermore, hydroboration-oxidation following the Cu-catalyzed AAA leads to the corresponding homochiral γ-alkyl-substituted alcohols. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23962149/Synthesis_of_optically_active_β__or_γ_alkyl_substituted_alcohols_through_copper_catalyzed_asymmetric_allylic_alkylation_with_organolithium_reagents_ L2 - https://doi.org/10.1021/jo401536u DB - PRIME DP - Unbound Medicine ER -