Z-Selective Copper-Catalyzed Asymmetric Allylic Alkylation with Grignard Reagents

Massimo Giannerini; Martin Fananas-Mastral; Ben L. Feringa; Martín Fañanás-Mastral

doi:10.1021/ja300743t

Z-Selective Copper-Catalyzed Asymmetric Allylic Alkylation with Grignard Reagents

Massimo Giannerini
, Martin Fananas-Mastral
, Ben L. Feringa^*
, Martín Fañanás-Mastral

^*Corresponding author for this work

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

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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.

Original language	English
Pages (from-to)	4108-4111
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	9
DOIs	https://doi.org/10.1021/ja300743t
Publication status	Published - 7-Mar-2012

Keywords

CROSS-COUPLING REACTIONS
MEDIATED SUBSTITUTION-REACTIONS
DOUBLE-BOND CONFIGURATION
RING-CLOSING METATHESIS
ARYL CHLORIDES
ENANTIOSELECTIVE ALLYLATION
STEREOSELECTIVE-SYNTHESIS
CONJUGATE ADDITION
SUZUKI COUPLINGS
MURAHASHI METHOD

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@article{c06366023f2b496781b751b5df46b535,

title = "Z-Selective Copper-Catalyzed Asymmetric Allylic Alkylation with Grignard Reagents",

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.",

keywords = "CROSS-COUPLING REACTIONS, MEDIATED SUBSTITUTION-REACTIONS, DOUBLE-BOND CONFIGURATION, RING-CLOSING METATHESIS, ARYL CHLORIDES, ENANTIOSELECTIVE ALLYLATION, STEREOSELECTIVE-SYNTHESIS, CONJUGATE ADDITION, SUZUKI COUPLINGS, MURAHASHI METHOD",

author = "Massimo Giannerini and Martin Fananas-Mastral and Feringa, \{Ben L.\} and Mart{\'i}n Fa{\~n}an{\'a}s-Mastral",

note = "PT: J; TC: 4; UT: WOS:000301550800046",

year = "2012",

month = mar,

day = "7",

doi = "10.1021/ja300743t",

language = "English",

volume = "134",

pages = "4108--4111",

journal = "Journal of the American Chemical Society",

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TY - JOUR

T1 - Z-Selective Copper-Catalyzed Asymmetric Allylic Alkylation with Grignard Reagents

AU - Giannerini, Massimo

AU - Fananas-Mastral, Martin

AU - Feringa, Ben L.

AU - Fañanás-Mastral, Martín

N1 - PT: J; TC: 4; UT: WOS:000301550800046

PY - 2012/3/7

Y1 - 2012/3/7

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.

AB - 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.

KW - CROSS-COUPLING REACTIONS

KW - MEDIATED SUBSTITUTION-REACTIONS

KW - DOUBLE-BOND CONFIGURATION

KW - RING-CLOSING METATHESIS

KW - ARYL CHLORIDES

KW - ENANTIOSELECTIVE ALLYLATION

KW - STEREOSELECTIVE-SYNTHESIS

KW - CONJUGATE ADDITION

KW - SUZUKI COUPLINGS

KW - MURAHASHI METHOD

U2 - 10.1021/ja300743t

DO - 10.1021/ja300743t

M3 - Article

SN - 0002-7863

VL - 134

SP - 4108

EP - 4111

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 9

ER -

Z-Selective Copper-Catalyzed Asymmetric Allylic Alkylation with Grignard Reagents

Abstract

Keywords

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