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- Title
Synthesis and Reactivity of π-Electron-Deficient (Arylsulfonyl)acetates.
- Authors
Alonso, Diego A.; Nájera, Carmen; Varea, Montserrat
- Abstract
Different π-electron-deficient (arylsulfonyl)acetates 9 were synthesized ( Scheme 1, Table 1), and their behavior as soft nucleophiles in the dialkylation reaction under phase-transfer catalysis conditions was studied ( Schemes 2 and 3, Tables 2 and 3). The [3,5-bis(trifluoromethyl)phenyl]sulfonyl group was shown to be the best substituent for the stereoselective synthesis of ( E)-aconitates 18 via an alkylation hydro-sulfonyl-elimination integrated process under very mild phase-transfer-catalysis conditions ( Scheme 5, Table 4). Sulfonylacetates 9h, i also underwent smooth Diels-Alder reactions with acyclic and cyclic dienes via in situ formation of the appropriate dienophile through a Knoevenagel condensation with paraformaldehyde ( Scheme 6). Reductive desulfonylation with Zn and NH4Cl in THF was shown to be an efficient method for removal of the synthetically useful sulfonyl moiety ( Scheme 7).
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 12, p4287
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.200290013