Papers

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
  • Hidemitsu Uno
  • ,
  • Ken Ichi Goto
  • ,
  • Noriko Watanabe
  • ,
  • Hitomi Suzuki

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
DOI
https://doi.org/10.1039/a705391f
CiNii Articles
http://ci.nii.ac.jp/naid/80004447465
URL
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=37049087325&origin=inward
ID information
  • DOI : 10.1039/a705391f
  • ISSN : 1472-7781
  • CiNii Articles ID : 80004447465
  • SCOPUS ID : 37049087325

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