Iterative catalyst controlled diastereodivergent synthesis of polypropionates

D. Roke; M. Fananas-Mastral; B. L. Feringa

doi:10.1039/c6qo00199h

Iterative catalyst controlled diastereodivergent synthesis of polypropionates

D. Roke, M. Fananas-Mastral, B. L. Feringa

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

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Abstract

Polypropionate fragments are synthesized using a combination of a copper-catalyzed asymmetric allylic alkylation, ruthenium-catalyzed cross-metathesis and iridium-catalyzed asymmetric allylic etherification. The use of an appropriate chiral ligand for each catalytic reaction allows access to 1,2-hydroxymethyl arrays with good to excellent control over the relative and absolute configuration of the different stereocenters.

Original language	English
Pages (from-to)	1383-1391
Number of pages	9
Journal	Organic Chemistry Frontiers
Volume	3
Issue number	11
DOIs	https://doi.org/10.1039/c6qo00199h
Publication status	Published - 2016

Keywords

ASYMMETRIC ALLYLIC SUBSTITUTION
ENANTIOSELECTIVE TOTAL-SYNTHESIS
QUATERNARY STEREOGENIC CENTERS
RING-CLOSING METATHESIS
GRIGNARD-REAGENTS
STEREOSELECTIVE-SYNTHESIS
ALDOL REACTION
ACYCLIC STEREOSELECTION
ORGANOLITHIUM REAGENTS
CONFORMATION DESIGN

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10.1039/c6qo00199h

Iterative catalyst controlled diastereodivergent synthesis of polypropionatesFinal publisher's version, 855 KBLicence: Taverne

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title = "Iterative catalyst controlled diastereodivergent synthesis of polypropionates",

abstract = "Polypropionate fragments are synthesized using a combination of a copper-catalyzed asymmetric allylic alkylation, ruthenium-catalyzed cross-metathesis and iridium-catalyzed asymmetric allylic etherification. The use of an appropriate chiral ligand for each catalytic reaction allows access to 1,2-hydroxymethyl arrays with good to excellent control over the relative and absolute configuration of the different stereocenters.",

keywords = "ASYMMETRIC ALLYLIC SUBSTITUTION, ENANTIOSELECTIVE TOTAL-SYNTHESIS, QUATERNARY STEREOGENIC CENTERS, RING-CLOSING METATHESIS, GRIGNARD-REAGENTS, STEREOSELECTIVE-SYNTHESIS, ALDOL REACTION, ACYCLIC STEREOSELECTION, ORGANOLITHIUM REAGENTS, CONFORMATION DESIGN",

author = "D. Roke and M. Fananas-Mastral and Feringa, {B. L.}",

year = "2016",

doi = "10.1039/c6qo00199h",

language = "English",

volume = "3",

pages = "1383--1391",

journal = "Organic Chemistry Frontiers",

issn = "2052-4129",

publisher = "ROYAL SOC CHEMISTRY",

number = "11",

}

TY - JOUR

T1 - Iterative catalyst controlled diastereodivergent synthesis of polypropionates

AU - Roke, D.

AU - Fananas-Mastral, M.

AU - Feringa, B. L.

PY - 2016

Y1 - 2016

N2 - Polypropionate fragments are synthesized using a combination of a copper-catalyzed asymmetric allylic alkylation, ruthenium-catalyzed cross-metathesis and iridium-catalyzed asymmetric allylic etherification. The use of an appropriate chiral ligand for each catalytic reaction allows access to 1,2-hydroxymethyl arrays with good to excellent control over the relative and absolute configuration of the different stereocenters.

AB - Polypropionate fragments are synthesized using a combination of a copper-catalyzed asymmetric allylic alkylation, ruthenium-catalyzed cross-metathesis and iridium-catalyzed asymmetric allylic etherification. The use of an appropriate chiral ligand for each catalytic reaction allows access to 1,2-hydroxymethyl arrays with good to excellent control over the relative and absolute configuration of the different stereocenters.

KW - ASYMMETRIC ALLYLIC SUBSTITUTION

KW - ENANTIOSELECTIVE TOTAL-SYNTHESIS

KW - QUATERNARY STEREOGENIC CENTERS

KW - RING-CLOSING METATHESIS

KW - GRIGNARD-REAGENTS

KW - STEREOSELECTIVE-SYNTHESIS

KW - ALDOL REACTION

KW - ACYCLIC STEREOSELECTION

KW - ORGANOLITHIUM REAGENTS

KW - CONFORMATION DESIGN

U2 - 10.1039/c6qo00199h

DO - 10.1039/c6qo00199h

M3 - Article

SN - 2052-4129

VL - 3

SP - 1383

EP - 1391

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 11

ER -

Iterative catalyst controlled diastereodivergent synthesis of polypropionates

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Keywords

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