A Passerini/Michael Pathway towards Butyrolactones

Shuanglong Jia; Laurent El Kaïm

doi:10.1002/ejoc.201800958

A Passerini/Michael Pathway towards Butyrolactones

Shuanglong Jia
, Laurent El Kaïm

Université Paris-Saclay

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

Abstract

The Passerini adducts of aromatic aldehydes may act as nucleophiles in Michael additions with acrylonitrile. The reaction proceeds together with hydrolysis of the ester. The resulting γ-hydroxynitrile may be cyclized under acidic conditions to afford a three-steps synthesis of γ-butyrolactones from isocyanides.

Original language	English
Pages (from-to)	6457-6464
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	46
DOIs	https://doi.org/10.1002/ejoc.201800958
Publication status	Published - 13 Dec 2018
Externally published	Yes

Keywords

Acrylonitrile
Bulticomponent reaction
Butyrolactone
Michael addition
Passerini reaction

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10.1002/ejoc.201800958

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title = "A Passerini/Michael Pathway towards Butyrolactones",

abstract = "The Passerini adducts of aromatic aldehydes may act as nucleophiles in Michael additions with acrylonitrile. The reaction proceeds together with hydrolysis of the ester. The resulting γ-hydroxynitrile may be cyclized under acidic conditions to afford a three-steps synthesis of γ-butyrolactones from isocyanides.",

keywords = "Acrylonitrile, Bulticomponent reaction, Butyrolactone, Michael addition, Passerini reaction",

author = "Shuanglong Jia and \{El Ka{\"i}m\}, Laurent",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = dec,

day = "13",

doi = "10.1002/ejoc.201800958",

language = "English",

volume = "2018",

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journal = "European Journal of Organic Chemistry",

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T1 - A Passerini/Michael Pathway towards Butyrolactones

AU - Jia, Shuanglong

AU - El Kaïm, Laurent

PY - 2018/12/13

Y1 - 2018/12/13

N2 - The Passerini adducts of aromatic aldehydes may act as nucleophiles in Michael additions with acrylonitrile. The reaction proceeds together with hydrolysis of the ester. The resulting γ-hydroxynitrile may be cyclized under acidic conditions to afford a three-steps synthesis of γ-butyrolactones from isocyanides.

AB - The Passerini adducts of aromatic aldehydes may act as nucleophiles in Michael additions with acrylonitrile. The reaction proceeds together with hydrolysis of the ester. The resulting γ-hydroxynitrile may be cyclized under acidic conditions to afford a three-steps synthesis of γ-butyrolactones from isocyanides.

KW - Acrylonitrile

KW - Bulticomponent reaction

KW - Butyrolactone

KW - Michael addition

KW - Passerini reaction

UR - https://www.scopus.com/pages/publications/85057328319

U2 - 10.1002/ejoc.201800958

DO - 10.1002/ejoc.201800958

M3 - Article

AN - SCOPUS:85057328319

SN - 1434-193X

VL - 2018

SP - 6457

EP - 6464

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 46

ER -

A Passerini/Michael Pathway towards Butyrolactones

Abstract

Keywords

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