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Paper | Special issue | Vol 99, No. 2, 2019, pp.1117-1127
Published online, 25th February, 2019
DOI: 10.3987/COM-18-S(F)82
The Effect of Lithium Ion on the Stereoselectivity of the Intramolecular Michael Addition of an N-Arylsulfoximine Anion

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

*Department of Chemistry, University of Missouri-Columbia, Columbia, MO 65211, USA.


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.