A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes

Darren J. Dixon; Mark S. Scott; Chris A. Luckhurst

doi:10.1055/s-2003-42470

A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes

Darren J. Dixon, Mark S. Scott, Chris A. Luckhurst

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

Abstract

A wide range of aldehydes was efficiently protected as pyrrole carbinol derivatives by direct addition of lithium pyrrolate in THF at -78°C. The protection is chemoselective towards aldehydes over ketones and the O-lithiated, O-protonated or O-silylated carbinols may be used to block the aldehyde from nucleophilic and basic reagents at low temperatures. Mild, basic deprotection using DBU, NaOMe or TBAF allows for in situ trapping-reactions (such as Wadsworth-Horner-Emmons olefination) of the released aldehyde.

Original language	English
Pages (from-to)	2317-2320
Number of pages	3
Journal	SYNLETT
Issue number	15
DOIs	https://doi.org/10.1055/s-2003-42470
Publication status	Published - 2003

Keywords

Aldehydes
Chemoselective
Protecting-group
Pyrrole carbinol
Tandem reactions

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10.1055/s-2003-42470

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title = "A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes",

abstract = "A wide range of aldehydes was efficiently protected as pyrrole carbinol derivatives by direct addition of lithium pyrrolate in THF at -78°C. The protection is chemoselective towards aldehydes over ketones and the O-lithiated, O-protonated or O-silylated carbinols may be used to block the aldehyde from nucleophilic and basic reagents at low temperatures. Mild, basic deprotection using DBU, NaOMe or TBAF allows for in situ trapping-reactions (such as Wadsworth-Horner-Emmons olefination) of the released aldehyde.",

keywords = "Aldehydes, Chemoselective, Protecting-group, Pyrrole carbinol, Tandem reactions",

author = "Dixon, {Darren J.} and Scott, {Mark S.} and Luckhurst, {Chris A.}",

year = "2003",

doi = "10.1055/s-2003-42470",

language = "English",

pages = "2317--2320",

journal = "SYNLETT",

issn = "1437-2096",

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T1 - A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes

AU - Dixon, Darren J.

AU - Scott, Mark S.

AU - Luckhurst, Chris A.

PY - 2003

Y1 - 2003

N2 - A wide range of aldehydes was efficiently protected as pyrrole carbinol derivatives by direct addition of lithium pyrrolate in THF at -78°C. The protection is chemoselective towards aldehydes over ketones and the O-lithiated, O-protonated or O-silylated carbinols may be used to block the aldehyde from nucleophilic and basic reagents at low temperatures. Mild, basic deprotection using DBU, NaOMe or TBAF allows for in situ trapping-reactions (such as Wadsworth-Horner-Emmons olefination) of the released aldehyde.

AB - A wide range of aldehydes was efficiently protected as pyrrole carbinol derivatives by direct addition of lithium pyrrolate in THF at -78°C. The protection is chemoselective towards aldehydes over ketones and the O-lithiated, O-protonated or O-silylated carbinols may be used to block the aldehyde from nucleophilic and basic reagents at low temperatures. Mild, basic deprotection using DBU, NaOMe or TBAF allows for in situ trapping-reactions (such as Wadsworth-Horner-Emmons olefination) of the released aldehyde.

KW - Aldehydes

KW - Chemoselective

KW - Protecting-group

KW - Pyrrole carbinol

KW - Tandem reactions

U2 - 10.1055/s-2003-42470

DO - 10.1055/s-2003-42470

M3 - Article

SN - 1437-2096

SP - 2317

EP - 2320

JO - SYNLETT

JF - SYNLETT

IS - 15

ER -

A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes

Abstract

Keywords

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