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Synlett 1992; 1992(11): 861-863
DOI: 10.1055/s-1992-21518
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Stereoselective Intramolecular [4+1] Cycloadditions with Germylenes

Laura A. Smith* , Eric J. Roskamp
  • *Department of Chemistry, Northwestern University, Evanston, Illinois 60208-3113, USA
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Publication Date:
08 March 2002 (online)

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The addition of germanium bis(bistrimethylsilyl)amide, Ge[N(TMS)2]2, to α,β-unsaturated, N-(3-hydroxypropyl)-imines leads to intramolecular [4+1] cycloadditions. The resulting bicyclic germanes are obtained in 68-88% yield. The product is obtained diastereoselectively when the imine is unsubstituted at the α-position: imines derived from α-methyl-α,β-unsaturated aldehydes give 1:1 mixtures of diastereomers. The relative stereochemistry of the diastereomers was established by NOE experiments. A bridging germanium alkoxide dimer is proposed to account for the observed change in diastereoselectivity.

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