New synthetic methodology for the synthesis of 7-substituted tetrahydroazepin-2-ones
- Resource Type
- Authors
- K. C. Russell; P. Andrew Evans; Andrew B. Holmes
- Source
- Journal of the Chemical Society, Perkin Transactions 1. :3397
- Subject
- Claisen rearrangement
chemistry.chemical_compound
Selenoxide elimination
chemistry
Aminal
Ketene
Organic chemistry
- Language
- ISSN
- 1364-5463
0300-922X
The Claisen rearrangement of the vinyl substituted ketene aminals 2(R = CH2CHMe2, CH2OSiButMe2) which were generated in situ by selenoxide elimination of the aminal precursors 3 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) furnished the enantiomerically pure 7-substituted tetrahydroazepin-2-ones 1.