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- W2893885850 endingPage "526" @default.
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- W2893885850 abstract "Sulfenic acid anions (RSO – ) represent an untapped functional group for the formation of sulfoxides and other organic compounds. Their stereoselective alkylation is an important component of this chemistry, but factors governing reaction outcomes are not fully understood. The current study uses Density Functional Theory methods to break down the influencing roles of substituents attached to 2‐aminoethanesulfenate. The lithium counterion can be coordinated to pendant ester or carbamate carbonyl groups, whereas the sulfenate oxygen readily participates in hydrogen bonding with proximal hydrogen atoms of the (protected) amino group. A Moc‐protected, ester substituted, 2‐aminoethanesulfenate adopts both lithium coordination and hydrogen bonding in the lowest energy form and demonstrates stereoselective methylation and benzylation consistent with experiments from the literature." @default.
- W2893885850 created "2018-10-05" @default.
- W2893885850 creator A5089755663 @default.
- W2893885850 date "2018-11-16" @default.
- W2893885850 modified "2023-09-30" @default.
- W2893885850 title "A Computational Determination of the Origins of Diastereoselective Alkylations of a Cysteinesulfenate Anion" @default.
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- W2893885850 doi "https://doi.org/10.1002/ejoc.201801053" @default.
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