Aminocyclanols, II: Stereochemical Studies on a New Ciramadol Analogue by NMR‐Spectroscopy | Zendy

Burgemeister Thomas | Zendy; Wiegrebe Wolfgang | Zendy; Ertan Mevlüt | Zendy; Akgün Hülya | Zendy; Özarslan Özdemir | Zendy

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Aminocyclanols, II: Stereochemical Studies on a New Ciramadol Analogue by NMR‐Spectroscopy

Author(s) -

Burgemeister Thomas,

Wiegrebe Wolfgang,

Ertan Mevlüt,

Akgün Hülya,

Özarslan Özdemir

Publication year - 1994

Publication title -

archiv der pharmazie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.468

H-Index - 61

eISSN - 1521-4184

pISSN - 0365-6233

DOI - 10.1002/ardp.19943271206

Subject(s) - chemistry , isopropyl , stereochemistry , menthone , nuclear magnetic resonance spectroscopy , pyrrolidine , stereoselectivity , organic chemistry , menthol , catalysis

The absol. configuration of a Ciramadol analogue obtained from (‐)‐menthone is established by 1 H‐NMR‐, simulated NMR‐, COSY‐90‐, and NOE‐measurements. The final compound 2‐(α‐1‐pyrrolidino)benzyl‐4‐isopropyl‐1‐methyl‐cyclohexan‐3‐one ( 4b ), e.g. , has 1 R ,2 S ,4 S ,11 S ‐configuration due to stereoselective Michael ‐type addition of pyrrolidine to the pertinent benzylidene intermediate 3 .

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