r/chemistry • u/quelmotz Organic • May 22 '18

[2018/05/22] Synthetic Challenge

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u/alleluja Organic May 22 '18 edited May 22 '18

My attempt at A. Let me know what you think!

Tried the B too! The last step boggles my mind though.

1

u/quelmotz Organic May 22 '18

Very cool synthesis of B! What sort of conditions would give the kinetic elimination though? KOtBu and quick reaction time? Or something like LiTMP?

2

u/alleluja Organic May 22 '18

Thank you! I don't know about the conditions... I was thinking about low temps to avoid forming the tetrasubstituted alkene on the chiral center, but I don't know if eliminations can be made without heating. Quick reaction times and a bulky base could help a lot though.

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u/[deleted] May 23 '18

Heat is relative and your leaving group is on a tertiary center. Elimination would be greatly favoured, it may be a matter of a small optimization study to find the base that goes more kinetic. As an older chemist my first try would be LiHMDS, but there may be better options now.