Palladium catalyzed stereospecific allylic substitution of 5- acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one by alcohols

Hanneke van der Deen; Arjan van Oeveren; Richard M. Kellogg; Bernard Feringa

doi:10.1016/S0040-4039(98)02683-5

Palladium catalyzed stereospecific allylic substitution of 5- acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one by alcohols

Hanneke van der Deen, Arjan van Oeveren, Richard M. Kellogg, Bernard Feringa

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Abstract

Enantiomerically pure 5-acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one are converted into 5-alkoxy-2(5H)-furanones and 6-alkoxy-2H-pyran-3(6H)-ones by a palladium catalyzed allylic substitution. The reactions proceed with nearly complete retention of configuration, resulting in products with ee’s of 95%.

Original language	English
Pages (from-to)	1755-1758
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(98)02683-5
Publication status	Published - 1999

Keywords

ENANTIOSELECTIVE SYNTHESIS
ABSOLUTE-CONFIGURATION
ASYMMETRIC-SYNTHESIS
GAMMA-LACTONES
TRANSESTERIFICATION
BUTENOLIDES
ADDITIONS
ETHERS

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title = "Palladium catalyzed stereospecific allylic substitution of 5- acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one by alcohols",

abstract = "Enantiomerically pure 5-acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one are converted into 5-alkoxy-2(5H)-furanones and 6-alkoxy-2H-pyran-3(6H)-ones by a palladium catalyzed allylic substitution. The reactions proceed with nearly complete retention of configuration, resulting in products with ee{\textquoteright}s of 95%.",

keywords = "ENANTIOSELECTIVE SYNTHESIS, ABSOLUTE-CONFIGURATION, ASYMMETRIC-SYNTHESIS, GAMMA-LACTONES, TRANSESTERIFICATION, BUTENOLIDES, ADDITIONS, ETHERS",

author = "Deen, {Hanneke van der} and Oeveren, {Arjan van} and Kellogg, {Richard M.} and Bernard Feringa",

note = "Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute",

year = "1999",

doi = "10.1016/S0040-4039(98)02683-5",

language = "English",

volume = "40",

pages = "1755--1758",

journal = "Tetrahedron Letters",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "9",

}

TY - JOUR

T1 - Palladium catalyzed stereospecific allylic substitution of 5- acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one by alcohols

AU - Deen, Hanneke van der

AU - Oeveren, Arjan van

AU - Kellogg, Richard M.

AU - Feringa, Bernard

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute

PY - 1999

Y1 - 1999

N2 - Enantiomerically pure 5-acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one are converted into 5-alkoxy-2(5H)-furanones and 6-alkoxy-2H-pyran-3(6H)-ones by a palladium catalyzed allylic substitution. The reactions proceed with nearly complete retention of configuration, resulting in products with ee’s of 95%.

AB - Enantiomerically pure 5-acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one are converted into 5-alkoxy-2(5H)-furanones and 6-alkoxy-2H-pyran-3(6H)-ones by a palladium catalyzed allylic substitution. The reactions proceed with nearly complete retention of configuration, resulting in products with ee’s of 95%.

KW - ENANTIOSELECTIVE SYNTHESIS

KW - ABSOLUTE-CONFIGURATION

KW - ASYMMETRIC-SYNTHESIS

KW - GAMMA-LACTONES

KW - TRANSESTERIFICATION

KW - BUTENOLIDES

KW - ADDITIONS

KW - ETHERS

U2 - 10.1016/S0040-4039(98)02683-5

DO - 10.1016/S0040-4039(98)02683-5

M3 - Article

VL - 40

SP - 1755

EP - 1758

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Palladium catalyzed stereospecific allylic substitution of 5- acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one by alcohols

Abstract

Keywords

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