The unstabilised Wittig reaction selectively forms cis alkenes
the verdict
SUPPORTED
the evidence backs this
confidence 90/100
The unstabilised Wittig reaction is well-known in organic chemistry for its selectivity in yielding cis (Z) alkenes via kinetic control.
Evidence for · 3
The modern interpretation of the Wittig reaction mechanism.
2013 · cited by 283
Reviews the mechanism of Wittig reactions and confirms that non-stabilized ylides operate under kinetic control to yield specific stereochemical outcomes.
See more details
More for · 2
Unequivocal experimental evidence for a unified lithium salt-free Wittig reaction mechanism for all phosphonium Ylide types: reactions with β-heteroatom-substituted aldehydes are consistently selective for cis-oxaphosphetane-derived products.
2012 · cited by 64
Demonstrates that Wittig reactions involving non-stabilized ylides consistently produce cis-oxaphosphetane-derived products under salt-free conditions.
Dissection of the mechanism of the Wittig reaction.
2019 · cited by 28
Details how the transition state of the salt-free Wittig reaction connects the initial C-C bond formation to the stereochemistry of the resulting alkene.