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DOI: 10.1055/s-0029-1218336
Diastereoselective
Thia-Claisen Rearrangement of Pyrrolidinone-Derived
Ketene N,S-Acetals
Publikationsverlauf
Publikationsdatum:
04. November 2009 (online)
The reactive conformations in Scheme 8 depicted the wrong absolute configuration of the substrates. The correct Scheme is shown below, with conformation I now giving rise to 17a and 17b, and conformation II leading to 18a and 18b.
![](https://www.thieme-connect.de/media/synlett/200918/r11809st.gif)
Scheme 8 Proposed reactive conformations of 16a (R = H) and 16b (R = Br)
The paragraph which begins ”In the case of brominated
intermediate 16b" should be replaced with
the following text:
”In the case of non-brominated
intermediate 16a, conformation I is slightly favored over II (possibly
due to the additional A¹,³-strain in
the latter conformation) and the major product is 17a.
For the brominated analogue 16b, it appears that
conformation II is strongly favored. The
reasons for this unexpected reversal in selectivity are currently
the subject of further investigation."
The authors thank Professor Donald Craig, Imperial College, for drawing their attention to this error.