- Generation and Characterization of Transient 3H-Indolium-methanides
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Transient 3H-indolium-methanides 3a-d have been generated from the corresponding 2-substituted 3H-indoles 1a-d by the N-(trimethylsilyl)methylation/desilylation method. 3a,b were trapped by dimethyl maleate and dimethyl fumarate stereospecifically.All ylides add dimethyl ethynedicarboxylate to form 9,9a-dihydro-3H-pyrroloindoles 11a-d, out of which 11c,d (R = 9a-alkoxy) readily eliminate the corresponding alkanols to form 12.In the absence of dipolarophiles, 1a is predominantly transformed into Fischer base 14, whereas 3b gives rise to an unsymmetrical dimer 16.
- Doepp, Dietrich,Rehmer, Gerd,Brueggemann, Helmut
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p. 1651 - 1656
(2007/10/02)
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