Tetrahedron

Synthesis and differential functionalisation of pyrrolidine and piperidine based spirodiamine scaffolds

K Weinberg, A Stoit, CG Kruse, MF Haddow…

Index: Weinberg, Kamil; Stoit, Axel; Kruse, Chris G.; Haddow, Mairi F.; Gallagher, Timothy Tetrahedron, 2013 , vol. 69, # 23 p. 4694 - 4707

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Citation Number: 6

Abstract

The synthesis and differential substitution/protection of a series of spirodiamine scaffolds are described. Methods for selective access to the two mono-N-methyl isomers based on 2, 7- diazaspiro [4.5] decane are also described. Key precursors associated with this chemistry are prone to rearrangement and methods for circumventing this issue are reported. While direct mono-carbamoylation (Boc) was not efficient, selective deprotection of doubly Boc- ...