A new multicomponent domino reaction of 1,3-dicarbonyl compounds: One-pot access to polycyclic N/O-, N/S-, and N/N-aminals

Organic Letters

Volumn 3, Issue 14, 2001, Pages 2145-2148

  Simon, Céline ^a   Peyronel, Jean François ^b   Rodriguez, Jean ^a  

^a Inst Mediterraneen d'Ecologie P   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; AMINE; HETEROCYCLIC COMPOUND; KETONE; PIPERIDONE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACROLEIN; AMINES; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PIPERIDONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 0035850297     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010056d     Document Type: Article

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42. The stereochemistry shown rests upon extensive NMR study including NOESY interactions, see Supporting Information.
43. Molecular models show that due to the rigid structure of the aromatic ring the approach leading to the fused aminal does not present an optimal C-O orbitals overlap.
44. The proposed stereochemistry for 6b is not yet elucidated but can be deducted by analogy with 6a.
45. Easily obtained by reaction of 1a with acrolein in the presence of Dowex resins: Simon, C. Ph.D. Thesis, in progress.
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