Acta Crystallographica Section C

Volume 65, Part 12 (December 2009)

organic compounds

 

Asymmetric ruthenium-catalysed [2+2] cycloadditions between bicyclic alkenes and chiral aryl-substituted acetylenic acyl camphorsultam alkynes

J. D. Goodreid, M. C. Jennings and W. Tam

Abstract: The regio- and absolute stereochemistry of (7S)-N-[4-(3-thienyl)tricyclo[4.2.1.0^2,5]non-3-en-3-ylcarbonyl]-2,10-camphorsultam tetrahydrofuran hemisolvate, C₂₄H₂₉NO₃S₂·0.5C₄H₈O, and (7S)-N-[4-(4-tolyl)tricyclo[4.2.1.0^2,5]non-3-en-3-ylcarbonyl]-2,10-camphorsultam, C₂₇H₃₃NO₃S, have been established. One contains a half-occupancy tetrahydrofuran solvent molecule located on a twofold axis and the other contains two crystallographically unique molecules which are nearly identical. The extended structures of both complexes can be explained via weak C-HO interactions, which link the molecules together into two-dimensional sheets in the ab plane for the thienyl complex and ultimately into a three-dimensional structure for the tolyl derivative. The stereochemistry of both structures confirms that [2+2] cycloadditions of bicyclic alkenes and alkynes catalysed by ruthenium are exclusively exo.

Formula: C₂₄H₂₉NO₃S₂·0.5C₄H₈O and C₂₇H₃₃NO₃S

	Structure factor file (CIF format) (206.2 kbytes) [ doi:10.1107/S0108270109045284/ga3134VIsup2.hkl ] Contains datablock VI
	Structure factor file (CIF format) (473.1 kbytes) [ doi:10.1107/S0108270109045284/ga3134VIIsup3.hkl ] Contains datablock VII

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