Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone. Application to the Synthesis of Z-Alkenoates and E,E-Dienoates

Lucile Anthore; Shiguang Li; Lorenzo V. White; Samir Z. Zard

doi:10.1021/acs.orglett.5b02681

Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone. Application to the Synthesis of Z-Alkenoates and E,E-Dienoates

Lucile Anthore
, Shiguang Li
, Lorenzo V. White
, Samir Z. Zard

Laboratoire de Synthèse Organique
McGill University

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

Abstract

A simple radical-based route to gem-α-dichloroketones, relying on the degenerative addition transfer of (S)-[3,3-dichloro-2-oxopropyl]-O-ethyl dithiocarbonate (xanthate), is described. The adducts can then be converted into Z-enoates by exposure to Et₃N in methanol. In the case of certain substrates, it was possible to form skipped dienoic acid and methyl E,E-dienoates.

Original language	English
Pages (from-to)	5320-5323
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.5b02681
Publication status	Published - 6 Nov 2015
Externally published	Yes

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title = "Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone. Application to the Synthesis of Z-Alkenoates and E,E-Dienoates",

abstract = "A simple radical-based route to gem-α-dichloroketones, relying on the degenerative addition transfer of (S)-[3,3-dichloro-2-oxopropyl]-O-ethyl dithiocarbonate (xanthate), is described. The adducts can then be converted into Z-enoates by exposure to Et3N in methanol. In the case of certain substrates, it was possible to form skipped dienoic acid and methyl E,E-dienoates.",

author = "Lucile Anthore and Shiguang Li and White, \{Lorenzo V.\} and Zard, \{Samir Z.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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doi = "10.1021/acs.orglett.5b02681",

language = "English",

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journal = "Organic Letters",

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T1 - Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone. Application to the Synthesis of Z-Alkenoates and E,E-Dienoates

AU - Anthore, Lucile

AU - Li, Shiguang

AU - White, Lorenzo V.

AU - Zard, Samir Z.

PY - 2015/11/6

Y1 - 2015/11/6

N2 - A simple radical-based route to gem-α-dichloroketones, relying on the degenerative addition transfer of (S)-[3,3-dichloro-2-oxopropyl]-O-ethyl dithiocarbonate (xanthate), is described. The adducts can then be converted into Z-enoates by exposure to Et3N in methanol. In the case of certain substrates, it was possible to form skipped dienoic acid and methyl E,E-dienoates.

AB - A simple radical-based route to gem-α-dichloroketones, relying on the degenerative addition transfer of (S)-[3,3-dichloro-2-oxopropyl]-O-ethyl dithiocarbonate (xanthate), is described. The adducts can then be converted into Z-enoates by exposure to Et3N in methanol. In the case of certain substrates, it was possible to form skipped dienoic acid and methyl E,E-dienoates.

U2 - 10.1021/acs.orglett.5b02681

DO - 10.1021/acs.orglett.5b02681

M3 - Article

AN - SCOPUS:84946763256

SN - 1523-7060

VL - 17

SP - 5320

EP - 5323

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone. Application to the Synthesis of Z-Alkenoates and E,E-Dienoates

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