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Z-Selective copper-catalyzed asymmetric allylic alkylation with Grignard reagents.
J Am Chem Soc. 2012 Mar 07; 134(9):4108-11.JA

Abstract

Allylic gem-dichlorides undergo regio- and enanantioselective (er up to 99:1) copper-catalyzed allylic alkylation with Grignard reagents affording chiral Z-vinyl chlorides. This highly versatile class of synthons can be subjected to Suzuki cross coupling affording optically active Z-alkenes and 1,3-cis,trans dienes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Giannerini M
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

AlkylationAllyl CompoundsCatalysisCopperHydrocarbons, ChlorinatedMolecular StructureOrganometallic CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22352853

Citation

Giannerini, Massimo, et al. "Z-Selective Copper-catalyzed Asymmetric Allylic Alkylation With Grignard Reagents." Journal of the American Chemical Society, vol. 134, no. 9, 2012, pp. 4108-11.
Giannerini M, Fañanás-Mastral M, Feringa BL. Z-Selective copper-catalyzed asymmetric allylic alkylation with Grignard reagents. J Am Chem Soc. 2012;134(9):4108-11.
Giannerini, M., Fañanás-Mastral, M., & Feringa, B. L. (2012). Z-Selective copper-catalyzed asymmetric allylic alkylation with Grignard reagents. Journal of the American Chemical Society, 134(9), 4108-11. https://doi.org/10.1021/ja300743t
Giannerini M, Fañanás-Mastral M, Feringa BL. Z-Selective Copper-catalyzed Asymmetric Allylic Alkylation With Grignard Reagents. J Am Chem Soc. 2012 Mar 7;134(9):4108-11. PubMed PMID: 22352853.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Z-Selective copper-catalyzed asymmetric allylic alkylation with Grignard reagents. AU - Giannerini,Massimo, AU - Fañanás-Mastral,Martín, AU - Feringa,Ben L, Y1 - 2012/02/27/ PY - 2012/2/23/entrez PY - 2012/2/23/pubmed PY - 2012/6/29/medline SP - 4108 EP - 11 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 134 IS - 9 N2 - Allylic gem-dichlorides undergo regio- and enanantioselective (er up to 99:1) copper-catalyzed allylic alkylation with Grignard reagents affording chiral Z-vinyl chlorides. This highly versatile class of synthons can be subjected to Suzuki cross coupling affording optically active Z-alkenes and 1,3-cis,trans dienes. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/22352853/Z_Selective_copper_catalyzed_asymmetric_allylic_alkylation_with_Grignard_reagents_ L2 - https://doi.org/10.1021/ja300743t DB - PRIME DP - Unbound Medicine ER -