Bioinspired metal-catalysed Doebner-Knoevenagel condensations between malonic acid half thioesters and aldehydes

Fabrice Berrué; Sylvain Antoniotti; Olivier P. Thomas; Philippe Amade

doi:10.1002/ejoc.200600880

Bioinspired metal-catalysed Doebner-Knoevenagel condensations between malonic acid half thioesters and aldehydes

Fabrice Berrué
, Sylvain Antoniotti
, Olivier P. Thomas
, Philippe Amade

UMR 6001 CNRS

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

20 Citations (Scopus)

Abstract

Inspired by polyketide biosynthesis, unprecedented metal-catalysed Doebner-Knoevenagel condensations between Malonic Acid Half Thioesters (MAHTs) and various aldehydes have been achieved through the use of Yb(OTf)₃ as catalyst, mimicking a five-domain polyketide synthase module for the first time. In the presence of 5-methoxybenzimidazole, stereo- and regiocontrol of the reaction proved to be high.

Original language	English
Pages (from-to)	1743-1748
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	11
DOIs	https://doi.org/10.1002/ejoc.200600880
Publication status	Published - 2007
Externally published	Yes

Keywords

Biomimetic synthesis
Knoevenagel condensation
Metal catalysis
Polyketides

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10.1002/ejoc.200600880

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title = "Bioinspired metal-catalysed Doebner-Knoevenagel condensations between malonic acid half thioesters and aldehydes",

abstract = "Inspired by polyketide biosynthesis, unprecedented metal-catalysed Doebner-Knoevenagel condensations between Malonic Acid Half Thioesters (MAHTs) and various aldehydes have been achieved through the use of Yb(OTf)3 as catalyst, mimicking a five-domain polyketide synthase module for the first time. In the presence of 5-methoxybenzimidazole, stereo- and regiocontrol of the reaction proved to be high.",

keywords = "Biomimetic synthesis, Knoevenagel condensation, Metal catalysis, Polyketides",

author = "Fabrice Berru{\'e} and Sylvain Antoniotti and Thomas, \{Olivier P.\} and Philippe Amade",

year = "2007",

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T1 - Bioinspired metal-catalysed Doebner-Knoevenagel condensations between malonic acid half thioesters and aldehydes

AU - Berrué, Fabrice

AU - Antoniotti, Sylvain

AU - Thomas, Olivier P.

AU - Amade, Philippe

PY - 2007

Y1 - 2007

N2 - Inspired by polyketide biosynthesis, unprecedented metal-catalysed Doebner-Knoevenagel condensations between Malonic Acid Half Thioesters (MAHTs) and various aldehydes have been achieved through the use of Yb(OTf)3 as catalyst, mimicking a five-domain polyketide synthase module for the first time. In the presence of 5-methoxybenzimidazole, stereo- and regiocontrol of the reaction proved to be high.

AB - Inspired by polyketide biosynthesis, unprecedented metal-catalysed Doebner-Knoevenagel condensations between Malonic Acid Half Thioesters (MAHTs) and various aldehydes have been achieved through the use of Yb(OTf)3 as catalyst, mimicking a five-domain polyketide synthase module for the first time. In the presence of 5-methoxybenzimidazole, stereo- and regiocontrol of the reaction proved to be high.

KW - Biomimetic synthesis

KW - Knoevenagel condensation

KW - Metal catalysis

KW - Polyketides

UR - https://www.scopus.com/pages/publications/34250642402

U2 - 10.1002/ejoc.200600880

DO - 10.1002/ejoc.200600880

M3 - Article

AN - SCOPUS:34250642402

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 11

ER -

Bioinspired metal-catalysed Doebner-Knoevenagel condensations between malonic acid half thioesters and aldehydes

Abstract

Keywords

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