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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

✍ Scribed by Anna M. Piątek; Agnieszka Chojnacka; Christian Chapuis; Janusz Jurczak

Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
167 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The now corrected X‐ray structure of (2__R__)‐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 (2__R__)‐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 TiCl~4~‐mediated and uncatalyzed conditions. The determining influence of these factors is rationalized by the loss of the masked C~2~ 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.

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