Chemoselectivity issues of the asymmetric interaction between cyclohexanone, β‐nitrostyrene, and benzoic acid under 5‐aryl prolinate's organocatalysis

4‐l‐menthyloxycarbonyl 5‐aryl prolinates were studied as organocatalysts of a novel three‐component reaction of cyclohexanone, benzoic acid, and β‐nitrostyrene. The presence of ortho‐halogen atom in 5‐aryl fragment of the catalyst is favored for driving the formation of chiral 7a‐hydroxyoctahydro‐2H...

Full description

Saved in:
Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2020-06, Vol.32 (6), p.833-841
Main Authors: Ivantcova, Polina M., Kudryavtsev, Konstantin V.
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzoic acid
Benzoic Acid - chemistry
Catalysis
Catalysts
Chlorine
Conjugation
Cyclohexanone
Cyclohexanones - chemistry
enamine catalysis
Molecular Structure
multicomponent reactions
proline
Stereoisomerism
Styrenes - chemistry
β‐peptides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:4‐l‐menthyloxycarbonyl 5‐aryl prolinates were studied as organocatalysts of a novel three‐component reaction of cyclohexanone, benzoic acid, and β‐nitrostyrene. The presence of ortho‐halogen atom in 5‐aryl fragment of the catalyst is favored for driving the formation of chiral 7a‐hydroxyoctahydro‐2H‐indol‐2‐one scaffold. 5‐(o‐Chlorophenyl) prolinate selectively afforded 3‐phenyl‐7a‐hydroxyoctahydro‐2H‐indol‐2‐one with ee 63%, whereas 5‐phenyl prolinate led to conjugation of β‐nitrostyrene to cyclohexanone (the Michael adduct). Plausible chlorine effect is accounted for the specific interaction of the 5‐aryl prolinate enamine intermediate with β‐nitrostyrene in the transition state.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23212