ChemInform Abstract: The Asymmetric Cyclocondensation Reaction of 1-Methoxy-3-silyloxybuta- 1,3-dienes with N-Glyoxyloyl-(2R)-bornane-10,2-sultam.
β Scribed by J. JURCZAK; A. JEZEWSKI
- Book ID
- 112038178
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 29 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0931-7597
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π SIMILAR VOLUMES
The asymmetric ene reaction of N-glyoxyloyl-(2R)-bomane-10,2-sultam 2 and its hemiacetal 3 with 1-pentene 4 and 1-hexene 5 in the presence of Lewis acids is reported. All the ene reactions studied led to diastereoisomeric mixtures of olefins 6 and 7 or 8 and 9, with predominance of products of the (
## ~ -~~~ Starting from sultam 1, the chiral dienophile (2R)-N-glyoxyloylbornane-lO,2-sultam (4) was readily prepared. Non-catalyzed atmospheric-and high-pressure as well as [Eu(fod),]-promoted [4 + 21 cycloadditions of l-methoxybuta-l,3-diene (5) to chiral dienophile 4, leading with high asymmetr