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Topic: stereoselective Luche reduction of cyclohexenone  (Read 4376 times)

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Offline palauamine89

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stereoselective Luche reduction of cyclohexenone
« on: November 07, 2010, 08:23:18 AM »
Does Luche reduction of cyclohexenone give selectively the pseudoequatorial alcohol?

And if it does, is it because of lower gauche interactions in the resulting half-chair conformer or something else?

Offline discodermolide

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Re: stereoselective Luche reduction of cyclohexenone
« Reply #1 on: November 07, 2010, 12:06:39 PM »
Does Luche reduction of cyclohexenone give selectively the pseudoequatorial alcohol?

And if it does, is it because of lower gauche interactions in the resulting half-chair conformer or something else?

yes and yes
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Offline Doc Oc

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Re: stereoselective Luche reduction of cyclohexenone
« Reply #2 on: November 07, 2010, 06:50:54 PM »
Actually, Luche reductions are not stereoselective in the absence of another controlling factor such as another stereocenter or a rigid cyclic structure that blocks one face of the ketone.  This has been demonstrated in many syntheses.

Offline MissPhosgene

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Re: stereoselective Luche reduction of cyclohexenone
« Reply #3 on: November 14, 2010, 10:46:04 PM »
Isn't it stereoselective in that the ring conformation determines the product spread?

I may be misunderstanding what you guys are saying.
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