A facile approach to the synthesis of allylic spiro ethers and lactones

Ming Chang P. Yeh; Yi Chin Lee; Tsao Ching Young

doi:10.1055/s-2006-950294

A facile approach to the synthesis of allylic spiro ethers and lactones

Ming Chang P. Yeh^*, Yi Chin Lee, Tsao Ching Young

^*Corresponding author for this work

Department of Chemistry

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

16 Citations (Scopus)

Abstract

Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones with diisobutylaluminum hydride at -78 °C followed by acid quenching furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)- substituted cycloalkenones generate spiro lactones upon reaction with sodium borohydride at 30 °C followed by acid quenching.

Original language	English
Pages (from-to)	3621-3624
Number of pages	4
Journal	Synthesis
Issue number	21
DOIs	https://doi.org/10.1055/s-2006-950294
Publication status	Published - 2006 Nov 3

Keywords

Enones
Heterocycles
Lactones
Spiro compounds

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-2006-950294

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title = "A facile approach to the synthesis of allylic spiro ethers and lactones",

abstract = "Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones with diisobutylaluminum hydride at -78 °C followed by acid quenching furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)- substituted cycloalkenones generate spiro lactones upon reaction with sodium borohydride at 30 °C followed by acid quenching.",

keywords = "Enones, Heterocycles, Lactones, Spiro compounds",

author = "Yeh, {Ming Chang P.} and Lee, {Yi Chin} and Young, {Tsao Ching}",

year = "2006",

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doi = "10.1055/s-2006-950294",

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AU - Yeh, Ming Chang P.

AU - Lee, Yi Chin

AU - Young, Tsao Ching

PY - 2006/11/3

Y1 - 2006/11/3

N2 - Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones with diisobutylaluminum hydride at -78 °C followed by acid quenching furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)- substituted cycloalkenones generate spiro lactones upon reaction with sodium borohydride at 30 °C followed by acid quenching.

AB - Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones with diisobutylaluminum hydride at -78 °C followed by acid quenching furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)- substituted cycloalkenones generate spiro lactones upon reaction with sodium borohydride at 30 °C followed by acid quenching.

KW - Enones

KW - Heterocycles

KW - Lactones

KW - Spiro compounds

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U2 - 10.1055/s-2006-950294

DO - 10.1055/s-2006-950294

M3 - Article

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EP - 3624

JO - Synthesis

JF - Synthesis

IS - 21

ER -

A facile approach to the synthesis of allylic spiro ethers and lactones

Abstract

Keywords

ASJC Scopus subject areas

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