Asymmetric Conjugate Addition of Grignard Reagents to Pyranones

Bin Mao; Martin Fananas Mastral; Ben L. Feringa

doi:10.1021/ol303141x

Asymmetric Conjugate Addition of Grignard Reagents to Pyranones

Bin Mao, Martin Fananas Mastral, Ben L. Feringa^*

^*Corresponding author for this work

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

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Abstract

An efficient enantioselective synthesis of lactones was developed based on the catalytic asymmetric conjugate addition (ACA) of alkyl Grignard reagents to pyranones. The use of 2H-pyran-2-one for the first time in the ACA with Grignard reagents allows for a variety of further transformations to access highly versatile building blocks such as beta-alkyl substituted aldehydes or beta-bromo-gamma-alkyl substituted alcohols with excellent regio- and stereoselectivity.

Original language	English
Pages (from-to)	286-289
Number of pages	4
Journal	Organic letters
Volume	15
Issue number	2
DOIs	https://doi.org/10.1021/ol303141x
Publication status	Published - 18-Jan-2013

Keywords

DIELS-ALDER REACTIONS
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
PHOSPHINE-PHOSPHITE LIGANDS
ENANTIOSELECTIVE SYNTHESIS
NATURAL-PRODUCTS
MICHAEL ADDITION
BASILIOLIDE B
2H-PYRAN-2-ONE
1,4-ADDITION
ALDEHYDES

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title = "Asymmetric Conjugate Addition of Grignard Reagents to Pyranones",

abstract = "An efficient enantioselective synthesis of lactones was developed based on the catalytic asymmetric conjugate addition (ACA) of alkyl Grignard reagents to pyranones. The use of 2H-pyran-2-one for the first time in the ACA with Grignard reagents allows for a variety of further transformations to access highly versatile building blocks such as beta-alkyl substituted aldehydes or beta-bromo-gamma-alkyl substituted alcohols with excellent regio- and stereoselectivity.",

keywords = "DIELS-ALDER REACTIONS, ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS, PHOSPHINE-PHOSPHITE LIGANDS, ENANTIOSELECTIVE SYNTHESIS, NATURAL-PRODUCTS, MICHAEL ADDITION, BASILIOLIDE B, 2H-PYRAN-2-ONE, 1,4-ADDITION, ALDEHYDES",

author = "Bin Mao and {Fananas Mastral}, Martin and Feringa, {Ben L.}",

note = "Relation: http://www.rug.nl/research/stratingh/ date_submitted:2013 Rights: University of Groningen, Stratingh Institute for Chemistry",

year = "2013",

month = jan,

day = "18",

doi = "10.1021/ol303141x",

language = "English",

volume = "15",

pages = "286--289",

journal = "Organic letters",

issn = "1523-7052",

publisher = "AMER CHEMICAL SOC INC",

number = "2",

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TY - JOUR

T1 - Asymmetric Conjugate Addition of Grignard Reagents to Pyranones

AU - Mao, Bin

AU - Fananas Mastral, Martin

AU - Feringa, Ben L.

N1 - Relation: http://www.rug.nl/research/stratingh/ date_submitted:2013 Rights: University of Groningen, Stratingh Institute for Chemistry

PY - 2013/1/18

Y1 - 2013/1/18

N2 - An efficient enantioselective synthesis of lactones was developed based on the catalytic asymmetric conjugate addition (ACA) of alkyl Grignard reagents to pyranones. The use of 2H-pyran-2-one for the first time in the ACA with Grignard reagents allows for a variety of further transformations to access highly versatile building blocks such as beta-alkyl substituted aldehydes or beta-bromo-gamma-alkyl substituted alcohols with excellent regio- and stereoselectivity.

AB - An efficient enantioselective synthesis of lactones was developed based on the catalytic asymmetric conjugate addition (ACA) of alkyl Grignard reagents to pyranones. The use of 2H-pyran-2-one for the first time in the ACA with Grignard reagents allows for a variety of further transformations to access highly versatile building blocks such as beta-alkyl substituted aldehydes or beta-bromo-gamma-alkyl substituted alcohols with excellent regio- and stereoselectivity.

KW - DIELS-ALDER REACTIONS

KW - ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS

KW - PHOSPHINE-PHOSPHITE LIGANDS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - NATURAL-PRODUCTS

KW - MICHAEL ADDITION

KW - BASILIOLIDE B

KW - 2H-PYRAN-2-ONE

KW - 1,4-ADDITION

KW - ALDEHYDES

U2 - 10.1021/ol303141x

DO - 10.1021/ol303141x

M3 - Article

SN - 1523-7052

VL - 15

SP - 286

EP - 289

JO - Organic letters

JF - Organic letters

IS - 2

ER -

Asymmetric Conjugate Addition of Grignard Reagents to Pyranones

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