Synthesis of (1R, 4R)-and (1S, 4S)-2, 5-diazabicyclo [2.2. 1] heptanes and their N-substituted derivatives

…, F Sauter, SM Siddiqi, B Küenburg, K Bhattacharya

Index: Jordis; Sauter; Siddiqi; Kuenburg; Bhattacharya Synthesis, 1990 , vol. 1, # 10 p. 925 - 930

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Citation Number: 33

Abstract

For the synthesis of the lR, 4R-enantiomer 4, we initially assumed that it would be suflicient to invert the con-figuration on carbon 2 of 2 and force the cyclization of the cis-tritosyl derivative 8. However, the desired (1R, 4R)-2, 5-diazabicyclo [2.2. 1] heptane derivative 9 could not be obtained by refluxing a toluene solution containing 8 with 3 equivalents of benzylamine. Follow-ing the suggestion of a reviewer we tried to achieve the in silu ...