Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 2-3, Pages 519-526Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201801053
Keywords
Sulfenates; Organosulfur compounds; Diastereoselectivity; Computational chemistry; Density functional calculations
Categories
Funding
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- University of Guelph
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available