Premium
1,2‐Carbonyl Transposition of a Protected Rubanone: Stereoselective synthesis of bicyclic and tricyclic lactams derived from quinidine
Author(s) -
Frackenpohl Jens,
Langer Peter,
Hoffmann H. Martin R.
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19980810551
Subject(s) - chemistry , bicyclic molecule , tricyclic , stereoselectivity , lactam , transposition (logic) , stereochemistry , halogenation , organic chemistry , catalysis , linguistics , philosophy
Abstract α‐Bromination of 9‐acetoxy rubanone 2 and subsequent reaction with secondary amines gave bicyclic α‐amino ketones as a kinetic product and a 4‐oxa‐1‐azatwistan‐2‐one 6 under thermodynamic conditions. This two‐step procedure represents a concise 1,2‐carbonyl transposition and provides a short route to lactam alkaloids.