Author(s)

Y. Elemes, K. W. Muir

ISBN

0108-2701

Publication year

2006

Periodical

Acta Crystallographica Section C-Crystal Structure Communications

Periodical Number

Volume

62

Pages

O458-O460

Author Address

Full version

Triazolidinediones react with each enantiomeric bornanesultam derivative of tiglic acid to produce the appropriate ene adduct in high yield and with excellent regioselectivity and diastereoselectivity. The optically pure products, viz. N-[(3R)-3-(4methyl-3,5-dioxo-1,2,4-triazolidin-1-yl)-2-methylenebutanoyl ](1S,2R)-bornane-10,2-sultam 0.15-hydrate, C(18)H(26)N(4)O(5)S(.)0.35H(2)O, and its enantiomer N-[(3S)-3-(4-methyl-3,5-dioxo1,2,4-triazolidin-1-yl)-2-methylenebutanoyl ]-(1R,2S)-bornane10,2-sultam0.35-hydrate, C(18)H(26)N(4)O(5)S(.)0.35H(2)O, have been characterized by spectroscopy and single- crystal X- ray analysis. Their structures are the result of C ss-re attack of the enophile on the double bond of the alkene.