Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents

Nathalie C. van der Molen; Theodora D. Tiemersma-Wegman; Martín Fañanás-Mastral; Ben L. Feringa

doi:10.1021/acs.joc.5b00371

Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents

Nathalie C. van der Molen, Theodora D. Tiemersma-Wegman, Martín Fañanás-Mastral, Ben L. Feringa

Research output: Contribution to journal › Article › Academic › peer-review

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Abstract

A highly efficient method for the copper-catalyzed asymmetric allylic alkylation of ortho-substituted cinnamyl bromides with Grignard reagents is reported. The use of a catalytic system comprising CuBr center dot SMe2 and TaniaPhos as chiral ligands gives rise to a range of branched products with excellent regio- and enantioselectivity.

Original language	English
Pages (from-to)	4981-4984
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	80
Issue number	10
DOIs	https://doi.org/10.1021/acs.joc.5b00371
Publication status	Published - 15-May-2015

Keywords

CONJUGATE ADDITION
CARBENE COMPLEXES
ARYLATION
CHLORIDES
HETEROCYCLES
LIGANDS

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10.1021/acs.joc.5b00371

Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of OrthoFinal publisher's version, 294 KBLicence: Taverne

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title = "Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents",

abstract = "A highly efficient method for the copper-catalyzed asymmetric allylic alkylation of ortho-substituted cinnamyl bromides with Grignard reagents is reported. The use of a catalytic system comprising CuBr center dot SMe2 and TaniaPhos as chiral ligands gives rise to a range of branched products with excellent regio- and enantioselectivity.",

keywords = "CONJUGATE ADDITION, CARBENE COMPLEXES, ARYLATION, CHLORIDES, HETEROCYCLES, LIGANDS",

author = "{van der Molen}, {Nathalie C.} and Tiemersma-Wegman, {Theodora D.} and Mart{\'i}n Fa{\~n}an{\'a}s-Mastral and Feringa, {Ben L.}",

year = "2015",

month = may,

day = "15",

doi = "10.1021/acs.joc.5b00371",

language = "English",

volume = "80",

pages = "4981--4984",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "AMER CHEMICAL SOC INC",

number = "10",

}

Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents. / van der Molen, Nathalie C.; Tiemersma-Wegman, Theodora D.; Fañanás-Mastral, Martín et al.
In: Journal of Organic Chemistry, Vol. 80, No. 10, 15.05.2015, p. 4981-4984.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents

AU - van der Molen, Nathalie C.

AU - Tiemersma-Wegman, Theodora D.

AU - Fañanás-Mastral, Martín

AU - Feringa, Ben L.

PY - 2015/5/15

Y1 - 2015/5/15

N2 - A highly efficient method for the copper-catalyzed asymmetric allylic alkylation of ortho-substituted cinnamyl bromides with Grignard reagents is reported. The use of a catalytic system comprising CuBr center dot SMe2 and TaniaPhos as chiral ligands gives rise to a range of branched products with excellent regio- and enantioselectivity.

AB - A highly efficient method for the copper-catalyzed asymmetric allylic alkylation of ortho-substituted cinnamyl bromides with Grignard reagents is reported. The use of a catalytic system comprising CuBr center dot SMe2 and TaniaPhos as chiral ligands gives rise to a range of branched products with excellent regio- and enantioselectivity.

KW - CONJUGATE ADDITION

KW - CARBENE COMPLEXES

KW - ARYLATION

KW - CHLORIDES

KW - HETEROCYCLES

KW - LIGANDS

U2 - 10.1021/acs.joc.5b00371

DO - 10.1021/acs.joc.5b00371

M3 - Article

C2 - 25902013

SN - 0022-3263

VL - 80

SP - 4981

EP - 4984

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 10

ER -

Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents

Abstract

Keywords

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