Hexafluoroacetone as a protecting and activating reagent. Regioselective esterification of aspartic, malic, and thiomalic acid

Ksenia Pumpor; Elisabeth Windeisen; Jan Spengler; Fernando Albericio; Klaus Burger

doi:10.1007/s00706-004-0183-9

Hexafluoroacetone as a protecting and activating reagent. Regioselective esterification of aspartic, malic, and thiomalic acid

Ksenia Pumpor, Elisabeth Windeisen, Jan Spengler, Fernando Albericio^*, Klaus Burger

^*Corresponding author for this work

Institute of Biochemistry

10 Citations (Scopus)

Abstract

Hexafluoroacetone reacts with α-functionalized α,β- dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.

Original language	English
Journal	Monatshefte fur Chemie
Volume	135
Issue number	11
Pages (from-to)	1427-1443
Number of pages	17
ISSN	0026-9247
DOIs	https://doi.org/10.1007/s00706-004-0183-9
Publication status	Published - 11.2004

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Academic Focus: Center for Infection and Inflammation Research (ZIEL)

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10.1007/s00706-004-0183-9

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abstract = "Hexafluoroacetone reacts with α-functionalized α,β- dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.",

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AU - Pumpor, Ksenia

AU - Windeisen, Elisabeth

AU - Spengler, Jan

AU - Albericio, Fernando

AU - Burger, Klaus

PY - 2004/11

Y1 - 2004/11

N2 - Hexafluoroacetone reacts with α-functionalized α,β- dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.

AB - Hexafluoroacetone reacts with α-functionalized α,β- dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.

UR - https://www.scopus.com/pages/publications/11144316824

U2 - 10.1007/s00706-004-0183-9

DO - 10.1007/s00706-004-0183-9

M3 - Journal articles

AN - SCOPUS:11144316824

SN - 0026-9247

VL - 135

SP - 1427

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JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 11

ER -

Hexafluoroacetone as a protecting and activating reagent. Regioselective esterification of aspartic, malic, and thiomalic acid

Abstract

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