Organozirconium-mediated solution-and solid-phase synthesis of 3-benzyl pyrrolidines and other potentially neuroactive amines

RA Hunter, DPS Macfarlane, RJ Whitby

Index: Hunter, Rupert A.; Macfarlane, Donald P. S.; Whitby, Richard J. Synlett, 2006 , # 19 p. 3314 - 3318

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Citation Number: 5

Abstract

The key step in our 3-benzylpyrrolidine synthesis was to be the zirconocene-mediated co-cyclisation of 1-aryl-4-aza-1,6-dienes 4. We needed a synthesis of 4, which was reasonable for library synthesis, including on a solid phase. The usual route, alkylation of an allylamine with a cinnamyl bromide, works well in solution but the large excess needed to drive the reaction to completion on a solid phase would lead to over-alkylation. It is also not suitable for library synthesis ...