- Synthesis and reactivity of π-electron-deficient (arylsulfonyl)acetates
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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).
- Alonso, Diego A.,Najera, Carmen,Varea, Montserrat
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p. 4287 - 4305
(2007/10/03)
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- π-Deficient α-arylsulfonyl esters as soft nucleophiles in organic synthesis
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Different π-deficient arylsulfonyl groups have been studied as candidates for the stabilization of α-sulfonyl esters. The 3,5-bis(trifluoromethyl)phenylsulfonyl group has been shown to be the best substituent for the stereoselective synthesis of E-aconitates by a dialkylation-dehydrosulfinylation integrated process under PTC conditions using K2CO3 as base.
- Alonso, Diego A.,Nájera, Carmen,Varea, Montserrat
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p. 8845 - 8848
(2007/10/03)
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