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Synthesis 1996; 1996(1): 145-148
DOI: 10.1055/s-1996-4173
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Enantioselective Synthesis of Bicyclic Tetrahydrofuran Carboxaldehydes from Chiral 3-Stannylbut-1-enyl Carbamates by Tandem Homoaldol/Aldol Reaction

Holger Paulsen, Claudia Graeve, Roland Fröhlich, Dieter Hoppe*
  • *Organisch-chemisches Institut der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany, Fax +49(251)839772
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Publication Date:
31 December 2000 (online)

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Enantioenriched 8-oxabicyclo[3.2.1]octane-6-carboxaldehydes were obtained by Lewis acid mediated homoaldol reaction of the (1Z,3R)-3-(tributylstannyl)but-1-enyl carbamate [(R)-7] with 1,5-diketones, followed by boron trifluoride mediated intramolecular aldol-type cyclization.

chiral annylstannanes - enantioselective homoaldol reaction - intramolecular Mukaiyama aldolization of 8-oxo-1-alkenyl carbamates 8-oxabicyclo[3.2.1]octane-6-carboxaldehydes

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