Abstract
New C-substituted derivatives of (1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptane were synthesized utilizing the directed metalation strategy. The absolute configuration of the 3substituted derivative rests on the comparison of the NMR spectra with a product of proven configurational assignment by X-ray crystallographic analysis.
Highlights
Various N-substituted derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane are known in the literature.[1]
Beak and Hoppe pioneered the directed lithiation of N-protected amines, 6 a procedure, which allows asymmetric induction in this step when the generally applicable secbutyllithium/(−)-sparteine system is employed for deprotonation. 7,8
In a recent communication we published the synthesis of novel C-substituted derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (1) (Scheme 1). This has been achieved by lithiation of the Boc-protected derivative 2 followed by the reaction with suitable electrophiles
Summary
Various N-substituted derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane are known in the literature.[1].
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