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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 3
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Original Articles

An Improved Procedure for the Synthesis of Chiral 2-Aza-Bicyclo[2.2.1]heptane

Pages 577-584 | Received 13 Jul 1995, Published online: 21 Aug 2006

References and Notes

  • Waldmann , H. 1994 . Synthesis , : 535 – 551 .
  • Larsen , S. D. and Grieco , P. A. 1985 . J. Am. Chem. Soc. , 107 : 1768 – 1769 .
  • Waldmann , H. 1988 . Angew. Chem. Int. Ed. Engl. , 27 : 274 – 275 .
  • Waldmann , H. 1989 . Liebigs Ann. Chem. , : 231 – 238 .
  • Pombo-Villar , E. , Boelsterli , J. , Cid , M. M. , France , J. , Fuchs , B. , Walkinshaw , M. and Weber , H.-P. 1993 . Helv. Chim. Acta , 76 : 1203 – 1215 .
  • It might seem confusing at first glance because the Sandoz group′s assignment is (1R,4R,1′S) for the desired hetero-Diels-Alder adduct (3). After the hydrogenation of the C5-C6 olefinic double bond, though, the priority rule demands a change in the assignment of the absolute configuration to (1S,4R,1′S) for the amines (1) and (5).
  • Malpass , J. R. and Tweddle , N. J. 1977 . J. Chem. Soc., Perkin Trans. 1 , : 874 – 884 .

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