Theoretical studies on chiral formamide-mediated asymmetric allylation of aldimines

The enantioselective allylation of simple aldimines has been studied making use of density functional theory calculations. The proposed reaction mechanism includes eight possible transition-state structures, four of them leading to the R and four to the S enantiomer, respectively. Despite the fact t...

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Bibliographic Details
Published inJournal of the Iranian Chemical Society Vol. 17; no. 3; pp. 623 - 630
Main Authors Yalalov, Denis A., Schmatz, Stefan
Format Journal Article
LanguageEnglish
Published Berlin/Heidelberg Springer Berlin Heidelberg 01.03.2020
Springer Nature B.V
Subjects
Allyl compounds
Analytical Chemistry
Biochemistry
Chemical reactions
Chemistry
Chemistry and Materials Science
Density functional theory
Enantiomers
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Reaction mechanisms
Stereoselectivity
Asymmetric allylation
Density functional calculations
Organic catalysis
Multiple transition-states
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Summary:The enantioselective allylation of simple aldimines has been studied making use of density functional theory calculations. The proposed reaction mechanism includes eight possible transition-state structures, four of them leading to the R and four to the S enantiomer, respectively. Despite the fact that this multiple transition-state problem depends on subtle effects, all density functionals and basis sets employed indicate that the R isomer is favourably formed in contradiction to earlier published experimental results. The discussion of the transition-state structures and the comparison with literature results give insight into the origin of the observed stereoselectivity. Graphic abstract
ISSN:1735-207X
1735-2428
DOI:10.1007/s13738-019-01795-z