Synthesis of C₂‐Symmetric 2,2′‐Bipyridines Derived from 4‐Substituted 1,10,10‐Trimethyl‐3‐oxa‐5‐aza‐tricyclo[5.2.1.0^2,6]decane

Abstract

Condensation of 2,2′‐bipyridinyl‐6,6′‐dicarboxaldehyde with 3‐butylamino‐1,7,7‐trimethyl‐bicyclo[2.2.1]heptan‐2‐ol affords the chiral, substituted bipyridine, bis‐6,6′‐{(1R,2S,4R,6R,7R)‐5‐butyl‐1,10,10‐trimethyl‐3‐oxa‐5‐aza‐tricyclo[5.2.1.0^2,6]dec‐4‐yl}‐2,2′‐bipyridine. The same compound is also produced via nickel‐catalyzed coupling of (1R,2S,4R,6R,7R)‐5‐butyl‐4‐(6‐bromo‐pyridin‐2‐yl)‐1,10,10‐trimethyl‐3‐oxa‐5‐aza‐tricyclo[5.2.1.0^2,6] decane.

Keywords:

• C ₂‐Symmetry
• 2,2′‐Bipyridines
• R‐Configuration
• S‐Configuration
• Asymmetric synthesis

Acknowledgments

Our gratitude to the EPSRC (Postdoctoral Fellowship GR/K13523 to S. R. D. and studentship to C. P. C.), the Nuffield Foundation (Undergraduate Bursary to M. T. G.), and the Institut Universitaire de Technologie, Lannion, France (M‐L. M.).