Synthesis of sparteine-like chiral diamines and evaluation in the enantioselective lithiation–substitution of N-(tert-butoxycarbonyl) pyrrolidine

…, JR Harrison, T Koplin, P O'Brien, J Parmene…

Index: Hermet, Jean-Paul R.; Porter, David W.; Dearden, Michael J.; Harrison, Justin R.; Koplin, Tobias; O'Brien, Peter; Parmene, Jerome; Tyurin, Vladimir; Whitwood, Adrian C.; Gilday, John; Smith, Neil M. Organic and Biomolecular Chemistry, 2003 , vol. 1, # 22 p. 3977 - 3988

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Citation Number: 71

Abstract

Three chiral diamines were synthesised and evaluated as sparteine surrogates in the lithiation–substitution of N-(tert-butoxycarbonyl) pyrrolidine. The synthesis and attempted resolution of sparteine-like diamines {(1S*, 2R*, 8R*)-10-methyl-6, 10-diazatricyclo [6.3. 1.02, 6] dodecane and (1S*, 2R*, 9R*)-11-methyl-7, 11-diazatricyclo [7.3. 1.02, 7] tridecane}(via inclusion complex formation) are reported. Unfortunately, it was only ...