Dec 1, 1989
Stepwise intramolecular cycloaddition of nitrile oxide equivalents derived from the Lewis acid-promoted reaction of 1-nitroalkadienes and allylic stannanes
Journal of the Chemical Society, Perkin Transactions 1
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- Volume
- Number
- 2
- First page
- 289
- Last page
- 295
- DOI
- 10.1039/a705391f
The Lewis acid-promoted reaction of 1-nitroalka-1,5-(or 1,6-)dienes with allylic stannanes has been studied. In the presence of TiCl4′ 1-nitrohexa-1,5-diene reacted smoothly with allyltrimethylstannane to give a diastereoisomeric mixture of 6-allyl-3a,4,5,6-tetrahydro-3H-cyclopent[c] isoxazoles, while the reaction using AlCl3 as catalyst led to an allylated cyclohexanone oxime derivative in good yield. The similar reaction of 1-nitrohepta-1,6-diene, however, gave a bicyclic dihydroisoxazole irrespective of the Lewis acids employed. In the latter case, nitrite oxide equivalents derived from 1-nitroalka-1,6-dienes underwent a stepwise cycloaddition as shown by the lack of stereospecificity in the reactions of (1E,6Z)-1-nitro-7- phenylhepta-1,6-diene and (1E,6Z)-1-nitro-octa-1,6-diene.
- Link information
- ID information
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- DOI : 10.1039/a705391f
- ISSN : 1472-7781
- CiNii Articles ID : 80004447465
- SCOPUS ID : 37049087325