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Synthesis 1998; 1998(2): 162-166
DOI: 10.1055/s-1998-2011
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Stereoselective Isoquinoline Alkaloid Synthesis with New Diselenides

Thomas Wirth* , Gianfranco Fragale
  • *Institut für Organische Chemie, Universität Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland; Fax + 41(61)2 67-11 05; E-mail: wirth@ubaclu.unibas.ch
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Publication History

Publication Date:
31 December 2000 (online)

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The synthesis of improved optically active selenium compounds for electrophilic additions to C=C double bonds is described. These reagents allow the formation of methoxyselenenylated products with high diastereoselectivities (up to 93% de). Intramolecular aminoselenenylations with chiral selenium electrophiles provide a short route to tetrahydroisoquinoline alkaloids.

asymmetric synthesis - chiral diselenides - chirality - isoquinoline alkaloids - selenium

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