Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene

Masayuki Iwasaki; Eiji Morita; Minoru Uemura; Hideki Yorimitsu; Koichiro Oshima

doi:10.1055/s-2006-956455

Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene

Masayuki Iwasaki, Eiji Morita, Minoru Uemura, Hideki Yorimitsu, Koichiro Oshima

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

18 Citations (Scopus)

Abstract

A new route to β,gamma;-unsaturated ketones is disclosed. Aryl pentamethylcyclopentadienyl ketones underwent allylation with allyldimethylaluminum to yield the corresponding alcohols. Heating the alcohols in boiling toluene resulted in removal of pentamethylcyclopentadiene to provide β,γ-unsaturated ketones. The removal would proceed via a retro-carbonyl-ene process. Synthesis of an alkyl allyl ketone is also described.

Original language	English
Pages (from-to)	167-169
Number of pages	3
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-2006-956455
Publication status	Published - Jan 4 2007
Externally published	Yes

Keywords

Allylation
Cleavage
Ketones
Pentamethylcyclopentadiene

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2006-956455

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title = "Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene",

abstract = "A new route to β,gamma;-unsaturated ketones is disclosed. Aryl pentamethylcyclopentadienyl ketones underwent allylation with allyldimethylaluminum to yield the corresponding alcohols. Heating the alcohols in boiling toluene resulted in removal of pentamethylcyclopentadiene to provide β,γ-unsaturated ketones. The removal would proceed via a retro-carbonyl-ene process. Synthesis of an alkyl allyl ketone is also described.",

keywords = "Allylation, Cleavage, Ketones, Pentamethylcyclopentadiene",

author = "Masayuki Iwasaki and Eiji Morita and Minoru Uemura and Hideki Yorimitsu and Koichiro Oshima",

year = "2007",

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doi = "10.1055/s-2006-956455",

language = "English",

pages = "167--169",

journal = "Synlett",

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T1 - Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene

AU - Iwasaki, Masayuki

AU - Morita, Eiji

AU - Uemura, Minoru

AU - Yorimitsu, Hideki

AU - Oshima, Koichiro

PY - 2007/1/4

Y1 - 2007/1/4

N2 - A new route to β,gamma;-unsaturated ketones is disclosed. Aryl pentamethylcyclopentadienyl ketones underwent allylation with allyldimethylaluminum to yield the corresponding alcohols. Heating the alcohols in boiling toluene resulted in removal of pentamethylcyclopentadiene to provide β,γ-unsaturated ketones. The removal would proceed via a retro-carbonyl-ene process. Synthesis of an alkyl allyl ketone is also described.

AB - A new route to β,gamma;-unsaturated ketones is disclosed. Aryl pentamethylcyclopentadienyl ketones underwent allylation with allyldimethylaluminum to yield the corresponding alcohols. Heating the alcohols in boiling toluene resulted in removal of pentamethylcyclopentadiene to provide β,γ-unsaturated ketones. The removal would proceed via a retro-carbonyl-ene process. Synthesis of an alkyl allyl ketone is also described.

KW - Allylation

KW - Cleavage

KW - Ketones

KW - Pentamethylcyclopentadiene

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DO - 10.1055/s-2006-956455

M3 - Article

AN - SCOPUS:33846414336

SN - 0936-5214

SP - 167

EP - 169

JO - Synlett

JF - Synlett

IS - 1

ER -

Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene

Abstract

Keywords

ASJC Scopus subject areas

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