Abstract
The stereochemical outcome of the intramolecular Michael addition of a sulfoximine carbanion to a Z-configured α,β-unsaturated ester is dependent on lithium ion coordination between the oxygen on the sulfoximine and the carbonyl oxygen of the ester, based on both experimental and computational studies. Formally, this leads to a more sterically congested structure than might otherwise be preferred. Indeed, addition of HMPA, a substance capable of effective solvation of lithium cations, changes the stereochemical course of the reaction dramatically.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1117-1127 |
| Number of pages | 11 |
| Journal | Heterocycles |
| Volume | 99 |
| Issue number | 2 |
| DOIs | |
| State | Published - 2019 |
Bibliographical note
Funding Information:This work was funded by the NIH (1RO1-AI59000-01 A1). Thanks to the Alexander von Humboldt Foundation for providing funds for a leave for MH at the Justus Liebig Universität (Giessen) in the laboratories of Professor Peter R. Schreiner, to whom we are also grateful.
Funding Information:
This work was funded by the NIH (1RO1-AI59000-01 A1). Thanks to the Alexander von Humboldt Foundation for providing funds for a leave for MH at the Justus Liebig Universit?t (Giessen) in the laboratories of Professor Peter R. Schreiner, to whom we are also grateful.
Publisher Copyright:
© 2019 The Japan Institute of Heterocyclic Chemistry Received