✦ LIBER ✦

Synthesis and Conformational Analysis of 3-Amino-2-decalones

✍ Scribed by Francois Piriou; Hugues d'Orchymont

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 616 KB
Volume: 34
Category: Article
ISSN: 0749-1581
DOI: 10.1002/(sici)1097-458x(199603)34:3<213::aid-omr868>3.0.co;2-a

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✦ Synopsis

A diastereoisomeric mixture of three 3-Z-amino-2-decalones (Z = benzyloxycarbonyl or carbobenzoxy) synthesized from 3-Boc-amino-1,2,3,4-tetrahydro-2-naphthalenol (Boc = tert-butyloxycarbonyl) was resolved by highperformance liquid chromatography on silica gel. For each isomer, the relative stereochemistry of chiral carbons and the conformation were assessed by 'H and NMR. In the three isomers, the Z-amino group adopts an equatorial orientation. Inversion of configuration of the a-amino chiral carbon induces a double chair inversion when the ring junction is cis, in order to keep the Z-amino group equatorial.

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