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Topic: mechanism  (Read 3008 times)

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Offline Snake

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mechanism
« on: October 15, 2006, 04:25:20 PM »
Hey guys.. i have this question which asks to show the mechanism with stereochemistry.. i don't know how to do it showing sterochemistry can anyone help pleasee..





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Re: mechanism
« Reply #1 on: October 15, 2006, 09:01:05 PM »
In this reaction you will make predominantly one diastereomer of product in favor of the other.  The idea of the question is to draw a transition state which explains why the one diastereomer is preferred.

Here is a hint: the diastereomers would arise from attack at one of the two faces of the cabonyl carbon.  How do you think the presence of the t-butyl group will affect these transition states?  It might not be an obvious steric interaction, but something which is a consequence of the arrangement of the t-butyl group in space (axial or equatorial).  Think about how that affects other substituents around the ring as well.

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