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Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes.
J Am Chem Soc. 2010 Mar 10; 132(9):2895-7.JA

Abstract

Copper-catalyzed allyl-alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete gamma- and E-selectivities and with preferential 1,3-anti stereochemistry. The reaction tolerates various functional groups in both the allylic phosphate and alkylborane. Catalytic mechanisms involving transmetalation between a trialkyl(alkoxo)borate and a copper(I) complex to form an alkylcopper(I) species are proposed.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ohmiya H
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan. ohmiya@sci.hokudai.ac.jp
Yokobori U
No affiliation info available
Makida Y
No affiliation info available
Sawamura M
No affiliation info available

MeSH

BoranesCatalysisCopperMolecular StructureOrganometallic CompoundsOrganophosphatesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20158189

Citation

Ohmiya, Hirohisa, et al. "Copper-catalyzed Gamma-selective Allyl-alkyl Coupling Between Allylic Phosphates and Alkylboranes." Journal of the American Chemical Society, vol. 132, no. 9, 2010, pp. 2895-7.
Ohmiya H, Yokobori U, Makida Y, et al. Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes. J Am Chem Soc. 2010;132(9):2895-7.
Ohmiya, H., Yokobori, U., Makida, Y., & Sawamura, M. (2010). Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes. Journal of the American Chemical Society, 132(9), 2895-7. https://doi.org/10.1021/ja9109105
Ohmiya H, et al. Copper-catalyzed Gamma-selective Allyl-alkyl Coupling Between Allylic Phosphates and Alkylboranes. J Am Chem Soc. 2010 Mar 10;132(9):2895-7. PubMed PMID: 20158189.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes. AU - Ohmiya,Hirohisa, AU - Yokobori,Umi, AU - Makida,Yusuke, AU - Sawamura,Masaya, PY - 2010/2/18/entrez PY - 2010/2/18/pubmed PY - 2010/6/15/medline SP - 2895 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 9 N2 - Copper-catalyzed allyl-alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete gamma- and E-selectivities and with preferential 1,3-anti stereochemistry. The reaction tolerates various functional groups in both the allylic phosphate and alkylborane. Catalytic mechanisms involving transmetalation between a trialkyl(alkoxo)borate and a copper(I) complex to form an alkylcopper(I) species are proposed. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20158189/Copper_catalyzed_gamma_selective_allyl_alkyl_coupling_between_allylic_phosphates_and_alkylboranes_ L2 - https://doi.org/10.1021/ja9109105 DB - PRIME DP - Unbound Medicine ER -