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 journalArticle

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 - Jan 1 2019

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