Homologation of α-hydroxy acids to α-unsubstituted β-hydroxy carboxamides via Arndt-Eistert reaction

Jan Spengler; Javier Ruíz-Rodríguez; Klaus Burger; Fernando Albericio

doi:10.1016/j.tetlet.2006.05.001

Homologation of α-hydroxy acids to α-unsubstituted β-hydroxy carboxamides via Arndt-Eistert reaction

Jan Spengler
, Javier Ruíz-Rodríguez
, Klaus Burger
, Fernando Albericio

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

7 Scopus citations

Abstract

Here we studied the homologation of leucic and phenyl lactic acid via Wolff-rearrangement of their diazoketones to the corresponding β-hydroxy acids. This reaction requires distinct conditions to that of their amino acid analogues. The choice of the O^α-substituent can selectively direct the reaction to α-unsubstituted β-hydroxy carboxamides or (E)-α,β-unsaturated carboxamides and offers a new route from α-hydroxy acids to such compounds.

Original language	English
Pages (from-to)	4557-4560
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	27
DOIs	https://doi.org/10.1016/j.tetlet.2006.05.001
State	Published - 3 Jul 2006
Externally published	Yes

Keywords

α,β-Unsaturated carboxylic acids
α-Hydroxy diazoketones
β-Hydroxy carboxylic acids
Microwave shock-heating

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10.1016/j.tetlet.2006.05.001

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title = "Homologation of α-hydroxy acids to α-unsubstituted β-hydroxy carboxamides via Arndt-Eistert reaction",

abstract = "Here we studied the homologation of leucic and phenyl lactic acid via Wolff-rearrangement of their diazoketones to the corresponding β-hydroxy acids. This reaction requires distinct conditions to that of their amino acid analogues. The choice of the Oα-substituent can selectively direct the reaction to α-unsubstituted β-hydroxy carboxamides or (E)-α,β-unsaturated carboxamides and offers a new route from α-hydroxy acids to such compounds.",

keywords = "α,β-Unsaturated carboxylic acids, α-Hydroxy diazoketones, β-Hydroxy carboxylic acids, Microwave shock-heating",

author = "Jan Spengler and Javier Ru{\'i}z-Rodr{\'i}guez and Klaus Burger and Fernando Albericio",

year = "2006",

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T1 - Homologation of α-hydroxy acids to α-unsubstituted β-hydroxy carboxamides via Arndt-Eistert reaction

AU - Spengler, Jan

AU - Ruíz-Rodríguez, Javier

AU - Burger, Klaus

AU - Albericio, Fernando

PY - 2006/7/3

Y1 - 2006/7/3

N2 - Here we studied the homologation of leucic and phenyl lactic acid via Wolff-rearrangement of their diazoketones to the corresponding β-hydroxy acids. This reaction requires distinct conditions to that of their amino acid analogues. The choice of the Oα-substituent can selectively direct the reaction to α-unsubstituted β-hydroxy carboxamides or (E)-α,β-unsaturated carboxamides and offers a new route from α-hydroxy acids to such compounds.

AB - Here we studied the homologation of leucic and phenyl lactic acid via Wolff-rearrangement of their diazoketones to the corresponding β-hydroxy acids. This reaction requires distinct conditions to that of their amino acid analogues. The choice of the Oα-substituent can selectively direct the reaction to α-unsubstituted β-hydroxy carboxamides or (E)-α,β-unsaturated carboxamides and offers a new route from α-hydroxy acids to such compounds.

KW - α,β-Unsaturated carboxylic acids

KW - α-Hydroxy diazoketones

KW - β-Hydroxy carboxylic acids

KW - Microwave shock-heating

UR - https://www.scopus.com/pages/publications/33744538320

U2 - 10.1016/j.tetlet.2006.05.001

DO - 10.1016/j.tetlet.2006.05.001

M3 - Artículo

AN - SCOPUS:33744538320

SN - 0040-4039

VL - 47

SP - 4557

EP - 4560

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 27

ER -

Homologation of α-hydroxy acids to α-unsubstituted β-hydroxy carboxamides via Arndt-Eistert reaction

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Keywords

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