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Synfacts 2007(10): 1029-1029  
DOI: 10.1055/s-2007-968979
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Heck/Diels-Alder Cascade Route to Tetrahydrocarbazoles

Contributor(s): Victor Snieckus, Wei Gan
H. Fuwa*, M. Sasaki*
Tohoku University, Sendai, Japan
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Publication History

Publication Date:
07 November 2007 (online)

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Significance

An unusual intramolecular Heck/­Diels-Alder cycloaddition conversion of α-phos­phono enecarbamates into tetrahydrocarbazoles and other nitrogen heterocycles is reported. The reaction undoubtedly proceeds via the in situ generated and unisolated indole-2,3-quinodimeth­anes, 2,3-dimethylenepyrrolidines, and 2,3-di­methylenepiperidine which, upon trapping with dienophiles, lead to the observed products. The starting materials are easily prepared by treating N-acetylcarba­mate with KHMDS and (PhO)2P(O)Cl.