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  4. Synthesis of Optically Active 5-Alkoxy-6-methylcyclohex-2-en-1-ones and 4-Alkoxy-5-methylcyclopent-1-enyl Benzoate
 
research article

Synthesis of Optically Active 5-Alkoxy-6-methylcyclohex-2-en-1-ones and 4-Alkoxy-5-methylcyclopent-1-enyl Benzoate

Turks, Maris  
•
Vogel, Pierre  
2009
The Journal of Organic Chemistry

The reaction of (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol benzoate with allyltrimethylsilane in SO,- and in the presence of a catalytic amount of Tf2NTMS gives a silyl sulfinate intermediate that furnishes (-)-(6Z,1'S,4S,5S)-5-methyl-4-(1'-phenylethoxy)octa-1,6-dien-6-yl benzoate after acidic workup. The latter undergoes ring-closing, metathesis producing (-)-(2S,3S)-2-methyl-3-((1S)-1-phenylethoxy)cyclopent-5-en-1-yl benzoate. It has been converted also into the corresponding trimethylsilyl enol ether. After oxidation, an enone is obtained that undergoes ring-closing metathesis giving (-)-(5S,6S)-6-methyl-5-((1S)-1-phenylethoxy)cyclohex-2-en-1-one.

  • Details
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Type
research article
DOI
10.1021/jo801981c
Web of Science ID

WOS:000262004000056

Author(s)
Turks, Maris  
Vogel, Pierre  
Date Issued

2009

Publisher

American Chemical Society

Published in
The Journal of Organic Chemistry
Volume

74

Start page

435

End page

437

Subjects

Olefin Metathesis Catalysts

•

Silyl Enol Ethers

•

Sulfur-Dioxide

•

19-Nor-1-Alpha,25-Dihydroxyvitamin D-3

•

Asymmetric-Synthesis

•

Bicyclic Lactams

•

Derivatives

•

5-(Tert-Butyldimethylsiloxy)-2-Cyclohexenone

•

Cyclohexenones

•

Methodology

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 30, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/60537
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