Catalytic enantioselective reformatsky reaction with ortho-substituted diarylketones

M. Angeles Fernandez-Ibanez; Beatriz Macia; Adriaan J. Minnaard; Ben L. Feringa

doi:10.1021/ol801574m

Catalytic enantioselective reformatsky reaction with ortho-substituted diarylketones

M. Angeles Fernandez-Ibanez
, Beatriz Macia
, Adriaan J. Minnaard
, Ben L. Feringa^*

^*Corresponding author for this work

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

45 Citations (Scopus)

22 Downloads (Pure)

Abstract

The catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones with good enantioselectivities and moderate to good yields is reported. A readily available BINOL derivative is used as a chiral catalyst, and the reactions are performed with ethyl iodoacetate as a nucleophile and Me(2)Zn as the zinc source. The presence of air was found to be crucial to achieve an effective C-C bond formation pointing to a radical mechanism.

Original language	English
Pages (from-to)	4041-4044
Number of pages	4
Journal	Organic letters
Volume	10
Issue number	18
DOIs	https://doi.org/10.1021/ol801574m
Publication status	Published - 18-Sept-2008

Keywords

RADICAL-ADDITION
NUCLEOPHILIC-ADDITION
ORGANIC-SYNTHESIS
DIMETHYLZINC-AIR
KETONES
ALDEHYDES
IMINES
ETHERS
DIETHYLZINC

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@article{0f75ca8e6a784ff8a39c00d3518ad77f,

title = "Catalytic enantioselective reformatsky reaction with ortho-substituted diarylketones",

abstract = "The catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones with good enantioselectivities and moderate to good yields is reported. A readily available BINOL derivative is used as a chiral catalyst, and the reactions are performed with ethyl iodoacetate as a nucleophile and Me(2)Zn as the zinc source. The presence of air was found to be crucial to achieve an effective C-C bond formation pointing to a radical mechanism.",

keywords = "RADICAL-ADDITION, NUCLEOPHILIC-ADDITION, ORGANIC-SYNTHESIS, DIMETHYLZINC-AIR, KETONES, ALDEHYDES, IMINES, ETHERS, DIETHYLZINC",

author = "Fernandez-Ibanez, \{M. Angeles\} and Beatriz Macia and Minnaard, \{Adriaan J.\} and Feringa, \{Ben L.\}",

year = "2008",

month = sep,

day = "18",

doi = "10.1021/ol801574m",

language = "English",

volume = "10",

pages = "4041--4044",

journal = "Organic letters",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

number = "18",

}

TY - JOUR

T1 - Catalytic enantioselective reformatsky reaction with ortho-substituted diarylketones

AU - Fernandez-Ibanez, M. Angeles

AU - Macia, Beatriz

AU - Minnaard, Adriaan J.

AU - Feringa, Ben L.

PY - 2008/9/18

Y1 - 2008/9/18

N2 - The catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones with good enantioselectivities and moderate to good yields is reported. A readily available BINOL derivative is used as a chiral catalyst, and the reactions are performed with ethyl iodoacetate as a nucleophile and Me(2)Zn as the zinc source. The presence of air was found to be crucial to achieve an effective C-C bond formation pointing to a radical mechanism.

AB - The catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones with good enantioselectivities and moderate to good yields is reported. A readily available BINOL derivative is used as a chiral catalyst, and the reactions are performed with ethyl iodoacetate as a nucleophile and Me(2)Zn as the zinc source. The presence of air was found to be crucial to achieve an effective C-C bond formation pointing to a radical mechanism.

KW - RADICAL-ADDITION

KW - NUCLEOPHILIC-ADDITION

KW - ORGANIC-SYNTHESIS

KW - DIMETHYLZINC-AIR

KW - KETONES

KW - ALDEHYDES

KW - IMINES

KW - ETHERS

KW - DIETHYLZINC

U2 - 10.1021/ol801574m

DO - 10.1021/ol801574m

M3 - Article

SN - 1523-7060

VL - 10

SP - 4041

EP - 4044

JO - Organic letters

JF - Organic letters

IS - 18

ER -

Catalytic enantioselective reformatsky reaction with ortho-substituted diarylketones

Abstract

Keywords

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