Cyclodec-2′-ynyl (1S,1′R)-(–)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate

Abstract

The synthesis and the crystal structure analysis via X‐ray diffraction of the title compound, C20H28O4, (I), are described. The title compound is a camphanic acid cyclo­decynyl ester. This compound contains a ten‐membered ring including a triple bond and is prepared by condensation of (1S)‐(−)‐camphanic acid chloride with (R)‐(+)‐cyclo­dec‐2‐yn‐1‐ol [(II), 90% ee]. This alcohol [Hanack & Wächter (1987). Chem. Ber. 120, 727–734] has been isolated by kinetic deracemization of the corresponding acetate [Zelder (2001). PhD Thesis. In preparation] with the lipase from mucor miehei. With this structure analysis, the configuration of (II) was determined.