✦ LIBER ✦
Intramolecular ring cleavage of chiral terpenoid-derived oxazinone via asymmetric anti-aldol reaction: Unexpected entry to a N-substituted tetrahydro-1,3-oxazine-2,4-dione derivative
✍ Scribed by Tariq R Abbas; J.I.G Cadogan; Allan A Doyle; Ian Gosney; Philip K.G Hodgson; Garnet E Howells; Alison N Hulme; Simon Parsons; Ian H Sadler
- Book ID
- 104257414
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 208 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
In the presence of excess Bu2BOTf to promote anti-selectivity, an asymmetric aldol reaction with a homochiral terpenoid-derived 1,3-oxazin-2-one as the chiral control element results unexpectedly in ring cleavage by an intramolecular process to form a N-substituted tetrahydro-l,3oxazine-2,4-dione in virtually quantitative yield.