| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - Enantiomerically Pure Highly Functionalized α-Amino Ketonesfrom the Reaction of Chiral Cyclic N-(9-Phenylfluoren-9-yl)α-Amido Esters with Organolithium Reagents
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - The reaction of methylN-(9-phenylfluoren-9-yl)pyroglutamate with severalorganolithium reagentsafforded the corresponding ketones in excellent yields and withcomplete retention of enantiomericpurity. The success of this transformation is due to the unusualstability of the tetrahedralintermediates 5, which stems from two factors: theelectron-withdrawing effect of the amide nitrogenand the lithium complexing ability of the fluorenyl ring of the9-phenylfluoren-9-yl group. Thisester-to-ketone transformation was also successfully applied tooxazolidinone 9 and imidazolidinone20 and provided a ketone (21b) that wasultimately transformed into the urea-lactam 26whichincorporates the bicyclic core of streptolidine lactam, a component ofthe streptrothricin antibiotics.
|
| article type
| |
| is part of this journal
| |
