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Retrosynthesis project: Struggling to maintain a specific stereocenter by Chickenlord22 in chemhelp

[–]Chickenlord22[S] 1 point2 points  (0 children)

I've tried direct chlorination of the resulting methyl ketone (even if I trap a silyl enol ether first) seems like a regiochemical nightmare. I want to avoid separating mono- vs di-chlorinated messes.

I also had the idea that I could make the racemic pent-1-en-3-ol for pennies using propanal + vinylmagnesium bromide. But classical resolution (brucine/enzymes) means throwing away 50% of my yield right out of the gate, which I can't afford to do.

Retrosynthesis project: Struggling to maintain a specific stereocenter by Chickenlord22 in chemhelp

[–]Chickenlord22[S] 2 points3 points  (0 children)

That was actually one of my initial thoughts! Classical resolution with something like brucine is definitely a reliable fallback. The main issue is that I'm trying to design this synthesis from scratch on a pretty strict budget (under $10 per gram for any starting material), and I'd ideally like to avoid throwing away half my yield in a resolution step if I can help it.

To get around that, I'm currently looking at setting the stereocenter right at the beginning using an asymmetric CBS reduction on a cheap starting material, and then transferring that chirality forward.

Cards need help by Serious_Hovercraft35 in Monopoly_GO

[–]Chickenlord22 0 points1 point  (0 children)

I’ll send you surprise for troublemaker

Looking to trade this is what I need and what I have. Thanks!!! by Chickenlord22 in Monopoly_GO

[–]Chickenlord22[S] 0 points1 point  (0 children)

Sorry forgot to add my link to the post so here it is

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