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- Title
Synthesis and [4+2] Cycloaddition of (2R,2′R)-N,N′-Fumaroylbis[fenchane-8,2-sultam] (=(2E)-1,4-Bis[(3aS,6S,7aR)-1,4,5,6,7,7a-hexahydro-7,7-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzothiazol-1-yl]but-2-ene-1,4-dione) to Cyclopentadiene.
- Authors
Anna 4;M. Piątek; Agnieszka Chojnacka; Christian Chapuis; Janusz Jurczak
- Abstract
The now corrected X-ray structure of (2R)-bornane-10,2-sultam ((−)-1a), as well as that of its already published N-crotonoyl derivative (−)-1d, were compared with those of the newly synthesized (2R)-fenchane-8,2-sultam ((+)-5a), as well as its N-crotonoyl derivative (−)-5d. Also the N-methyl- and N-acryloylfenchane-8,2-sultams (−)-5b,c were prepared, and both the reactivity and diastereoselectivity imparted by the new chiral auxiliary to N,N′-fumaroylbis[fenchane-8,2-sultam] (−)-5e were compared with those of (−)-1a by addition of cyclopenta-1,3-diene to (−)-5e, in various solvents and at different temperatures under TiCl4-mediated and uncatalyzed conditions. The determining influence of these factors is rationalized by the loss of the masked C2 symmetry earlier attributed to camphor-derived sultams as well as transition-state dipolar stabilization by the solvent of the thermodynamically less stable syn-s-cis conformer.
- Publication
Helvetica Chimica Acta, 2005, Vol 88, Issue 9, p2441
- ISSN
0018-019X
- Publication type
Article