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Copper-catalyzed enantioselective allylic substitution with alkylboranes.
J Am Chem Soc. 2012 Nov 14; 134(45):18573-6.JA

Abstract

The first catalytic enantioselective allylic substitution reaction with alkylboron compounds has been achieved. The reaction between alkyl-9-BBN reagents and primary allylic chlorides proceeded with excellent γ-selectivities and high enantioselectivities under catalysis of a Cu(I)-DTBM-SEGPHOS system. The protocol produces terminal alkenes with an allylic stereogenic center branched with functionalized sp(3)-alkyl groups. The reaction with a γ-silicon-substituted allyl chloride affords an efficient strategy for the enantioselective synthesis of functionalized α-stereogenic chiral allylsilanes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shido Y
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Japan.
Yoshida M
No affiliation info available
Tanabe M
No affiliation info available
Ohmiya H
No affiliation info available
Sawamura M
No affiliation info available

MeSH

AlkenesAllyl CompoundsBoranesCatalysisCopperMolecular StructureOrganometallic CompoundsSilanesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23106350

Citation

Shido, Yoshinori, et al. "Copper-catalyzed Enantioselective Allylic Substitution With Alkylboranes." Journal of the American Chemical Society, vol. 134, no. 45, 2012, pp. 18573-6.
Shido Y, Yoshida M, Tanabe M, et al. Copper-catalyzed enantioselective allylic substitution with alkylboranes. J Am Chem Soc. 2012;134(45):18573-6.
Shido, Y., Yoshida, M., Tanabe, M., Ohmiya, H., & Sawamura, M. (2012). Copper-catalyzed enantioselective allylic substitution with alkylboranes. Journal of the American Chemical Society, 134(45), 18573-6. https://doi.org/10.1021/ja3093955
Shido Y, et al. Copper-catalyzed Enantioselective Allylic Substitution With Alkylboranes. J Am Chem Soc. 2012 Nov 14;134(45):18573-6. PubMed PMID: 23106350.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-catalyzed enantioselective allylic substitution with alkylboranes. AU - Shido,Yoshinori, AU - Yoshida,Mika, AU - Tanabe,Masahito, AU - Ohmiya,Hirohisa, AU - Sawamura,Masaya, Y1 - 2012/10/31/ PY - 2012/10/31/entrez PY - 2012/10/31/pubmed PY - 2013/4/27/medline SP - 18573 EP - 6 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 134 IS - 45 N2 - The first catalytic enantioselective allylic substitution reaction with alkylboron compounds has been achieved. The reaction between alkyl-9-BBN reagents and primary allylic chlorides proceeded with excellent γ-selectivities and high enantioselectivities under catalysis of a Cu(I)-DTBM-SEGPHOS system. The protocol produces terminal alkenes with an allylic stereogenic center branched with functionalized sp(3)-alkyl groups. The reaction with a γ-silicon-substituted allyl chloride affords an efficient strategy for the enantioselective synthesis of functionalized α-stereogenic chiral allylsilanes. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/23106350/Copper_catalyzed_enantioselective_allylic_substitution_with_alkylboranes_ DB - PRIME DP - Unbound Medicine ER -