Elucidation of the stereochemistry of octahydroisoquinoline derivatives by NMR spectroscopy

Ghiviriga, Ion; Bottari, Patricia; Hudlický, Tomáš

doi:10.1002/(sici)1097-458x(199909)37:9<653::aid-mrc511>3.0.co;2-w

Search citation statements

Order By: Relevance

Paper Sections

Select...

Nmr Study and Stereochemistry1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2001

Publication Types

Select...

Article1

Relationship

Self Cite1

Independent0

Authors

Journals

Cited by 1 publication

(1 citation statement)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We have noticed similar NOE's in molecules which have the geometry of cis-decalin. 21 The proton spectra of the two 4,5,6-trisubstituted oxazines, 3j and 3o, each displayed signals for mixtures of isomers. In the case of 3o the mixture contained three isomers in a ratio 3oЈ-3oЉ-3oٞ of 1 : 0.58 : 0.25.…”

Section: Nmr Study and Stereochemistrymentioning

confidence: 99%

Stereochemical aspects of novel 5,6-dihydro-4H-1,3-oxazines

Katritzky

Ghiviriga

Chen

et al. 2001

J. Chem. Soc., Perkin Trans. 2

Self Cite

View full text Add to dashboard Cite

Novel polysubstituted 5,6-dihydro-4H-1,3-oxazines are synthesized by 1,4-cycloaddition of unactivated olefins with N-acyliminiums from benzotriazole precursors. The configuration and conformation of the products are deduced from NMR investigation. The regio-and exo-endo stereochemistry of the cycloaddition are discussed. Conformations of compounds of six types of substitution (6-mono; 6,6-, 5,6-and 4,6-di; 4,6,6-and 4,5,6-tri) are rationalized on the basis of axial-1,3-repulsion and the anomeric effect.

show abstract

Section: Nmr Study and Stereochemistrymentioning

confidence: 99%