The effect of lithium ion on the stereoselectivity of the intramolecular Michael addition of an N-aryl-sulfoximine anion

Aswin Garimalla, Quin Long, Christopher J. Cramer, Michael Harmata

Research output: Contribution to journalArticlepeer-review

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 languageEnglish (US)
Pages (from-to)1117-1127
Number of pages11
JournalHeterocycles
Volume99
Issue number2
DOIs
StatePublished - 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

Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.

Fingerprint Dive into the research topics of 'The effect of lithium ion on the stereoselectivity of the intramolecular Michael addition of an N-aryl-sulfoximine anion'. Together they form a unique fingerprint.

Cite this