JOURNAL ARTICLE
RESEARCH SUPPORT, N.I.H., EXTRAMURAL
Add like
Add dislike
Add to saved papers

Evans Enolates: Structures and Mechanisms Underlying the Aldol Addition of Oxazolidinone-Derived Boron Enolates.

The soft enolization of an acylated oxazolidinone using di-n-butylboron triflate (n-Bu2 BOTf) and trialkylamines and subsequent aldol addition was probed structurally and mechanistically using a combination of IR and NMR spectroscopies. None of the species along the reaction coordinate show a penchant for aggregating. Complexation of the acylated oxazolidinone by n-Bu2 BOTf was too rapid to monitor, as was the subsequent enolization with Et3 N (triethylamine). The preformed n-Bu2 BOTf·Et3 N complex, displaying muted Lewis acidity and affiliated tractable rates, reveals a rate-limiting complexation via a transition structure with a complicated counterion. n-Bu2 BOTf·i-Bu3 N bearing a hindered amine shifts the rate-limiting step to proton transfer. Rate studies show that the aldol addition with isobutyraldehyde occurs as proffered by others.

Full text links

We have located links that may give you full text access.
Can't access the paper?
Try logging in through your university/institutional subscription. For a smoother one-click institutional access experience, please use our mobile app.

For the best experience, use the Read mobile app

Mobile app image

Get seemless 1-tap access through your institution/university

For the best experience, use the Read mobile app

All material on this website is protected by copyright, Copyright © 1994-2024 by WebMD LLC.
This website also contains material copyrighted by 3rd parties.

By using this service, you agree to our terms of use and privacy policy.

Your Privacy Choices Toggle icon

You can now claim free CME credits for this literature searchClaim now

Get seemless 1-tap access through your institution/university

For the best experience, use the Read mobile app