(R_S)-(1R,2S,3R)-2-Methoxy-1,7,7-trimethyl-N-(4-nitrobenzylidene)bicyclo[2.2.1]heptane-3-sulfinamide

Abstract

The title compound was synthesized from (+)-camphor, and its structure determined. The absolute configuration was determined using the known configuration of (+)-camphor. CommentThe chiral N-sulfinyl imines are versatile intermediates in organic synthesis, particularly for preparation of amine derivatives. We have recently prepared (Rs)-N-[(1R,2S,3R)-2-methoxy-1,7,7-trimethylbicyclo[2,2,1]heptane-3-sulfinyl-p-nitrobenzal imine from ((1R)-3-exo-mercapto-2-exo-methoxy-1, 7, 7-trimethyl-bicyclo[2.2.1]heptane) which was prepared from (+)-camphor (Yang, Li et al., 1994; Yang, Chen et al., 1994). The absolute configuration was not determined by the value of Flack parameter [0.05(0.12)], but we determined its absolute configuration by C12 on the skeleton of camphor whose absolute configuration is known to be R.The absolute configurations of C8, C12 and C13 of the molecule are known as R, S, and R. So the absolute configuration of atom S of the molecule is R. The C8-S distance is 1.815 Å, S-O is 1.471Å and S-N1 is 1.710 Å. The C8-S-O1 angle is 105.8°, O1-S-N1 is 110.8° and C8-S-N1 is 94.8°.