Is it possible to perform reductive alkylation of the 4a/5 double bond of Wieland-Miescher ketone in an anti position, by adding allyl bromide to C-5 and Hydrogen on C-4a as shown in the equation attached? I have done a literature review and all that is reported is the syn addition.
I suggest to use the method published long ago by Prof. Gilbert Stork (Columbia university, US) that involve reaction with lithium in liquid ammonia followed by insitu allylation. Be aware of possible competing O-allylation.
If you need more detail email at [email protected]. Hope the best
Dear Professor Krief,
Thank you for your input, I have came across the alkylation using Lithium in liq. ammonia during my literature search. And I have noticed that the stereochemistry of the product would be different from what i need. I am talking about the C4a junction carbon, when using Li in liq. NH3 the reduction would result in C4a having S configuration, and a cis-decalin product. I want the C4a carbon to have R configuration after the reduction of the double bond, and the product to be trans decalin. Thermodynamically it seems that the product i want is less favored, the decalin would have more strain, but the natural product i want to synthesize (a diterpene pyrone) have that specific configuration. Your opinion is highly appreciated.
Regards,
Amjad
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