| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348679 | Tetrahedron: Asymmetry | 2006 | 6 Pages |
Abstract
The stereoselective preparation of a new Meyers' bicyclic lactam-bridged biaryl 1, highly structurally related to circumdatins, benzomalvins and asperlicins, is reported. Using the popular Meyers' diastereoselective lactamization, under dehydrating conditions (CH2Cl2/reflux/MgSO4), trans-(aS,R,S)-1 was obtained in a rather modest yield of 25% and an excellent diastereoselectivity >95%. An alternative procedure making use of the activating agents of carboxylic acid (Mukaiyama reagent and FEP) allowed the lactamization process to take place under milder conditions (CH2Cl2/20 °C) affording trans-(aS,R,S)-1 in fairly good yields (50%-85%) and in up to 65% de.
Related Topics
Physical Sciences and Engineering
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Inorganic Chemistry
Authors
Maël Penhoat, Pierre Bohn, Georges Dupas, Cyril Papamicaël, Francis Marsais, Vincent Levacher,