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Topic: Allylic alcohol, configuration inversion.  (Read 4607 times)

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Offline cundi

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Allylic alcohol, configuration inversion.
« on: September 02, 2010, 07:18:03 AM »
Hi guys
Could you suggest me any method for inverting the configuration of an allylic alcohol?
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Offline sjb

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Re: Allylic alcohol, configuration inversion.
« Reply #1 on: September 02, 2010, 08:13:12 AM »
Do you mean the double-bond geometry? E  :rarrow: Z (or vice versa), or e.g. (4R)-2-pentene-4-ol to (4S)-2-pentene-4-ol?
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Offline cundi

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Re: Allylic alcohol, configuration inversion.
« Reply #2 on: September 02, 2010, 10:38:43 AM »
Apologies,
I mean R -S configuration.
In my molecule i have not posibily of Z/E isomers; it is a terminal olefin.

See attached pdf

Thanks in advance
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Offline sjb

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Re: Allylic alcohol, configuration inversion.
« Reply #3 on: September 02, 2010, 12:55:12 PM »
Quote from: cundi on September 02, 2010, 10:38:43 AM
Apologies,
I mean R -S configuration.
In my molecule i have not posibily of Z/E isomers; it is a terminal olefin.

See attached pdf

Thanks in advance

Mitsunobu inversion? http://orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0607 or similar?
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Offline OC pro

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Re: Allylic alcohol, configuration inversion.
« Reply #4 on: September 02, 2010, 02:30:33 PM »
Mitsunobu on tertiary alcohols is difficult and will not work properly.
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Offline cundi

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Re: Allylic alcohol, configuration inversion.
« Reply #5 on: September 03, 2010, 02:46:42 AM »
I had already considered mitsunobu reaction! But as OC pro says, it doesn't wotk.
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Offline sjb

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Re: Allylic alcohol, configuration inversion.
« Reply #6 on: September 04, 2010, 12:27:46 PM »
Hmm, not really sure then - what does happen if you try the Mitsunobu conditions? How did you make the cyclic compound in the first place?
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