Uploaded May 2022 | Updated September 2026, 1 week ago

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In this episode, I discuss sulfur ylides and the Corey-Chaykovsky reaction, which forms epoxides, aziridines, as well as cyclopropanes.

On slide 8, I mistakenly say "the N parameters of ketones" but as aldehydes and ketones are electrophiles, I should have said "the E parameters".

On slide 10, the oxygen is missing from the sulfonium after addition.

Community Discord: discord.gg/QWNPETtPcZ

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Links to articles discussed in this episode:
N-parameter database - cup.lmu.de/oc/mayr/reaktionsdatenbank2
1st thioether arylation - doi.org/10.1021/ol990069f
2nd thioether arylation - doi.org/10.1246/bcsj.61.707
3rd thioether arylation - doi.org/10.1039/P19830002913
oxidation of sulfonium - doi.org/10.1248/cpb.c20-00132
1st epoxide - doi.org/10.1021/op3003085
2nd epoxide - doi.org/10.1016/j.ejmech.2017.10.063
isoindazole - doi.org/10.1007/s10593-020-02699-0
trifluoromethyl - doi.org/10.1039/C5CC04991A
1st cyclopropanation - doi.org/10.1002/chem.201101687
2nd cyclopropanation - doi.org/10.3390/molecules25040789
chiral thioether catalysts - doi.org/10.1021/ar030045f
Trost paper - doi.org/10.1021/ja00276a043
Trost Ylide prep - doi.org/10.15227/orgsyn.054.0027
1st Trost -doi.org/10.1021/ol103050c
2nd Trost - doi.org/10.1055/s-1998-1690
3rd Trost - doi.org/10.1021/ol101136a
4th Trost - doi.org/10.1021/ol301331t
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