Asymmetric Diels-Alder reactions of chiral (E)-2-cyanocinnamates with cyclopentadiene
Several chiral derivatives of (E)-2-cyanocinnamic acid are used as trisubstituied dienophiles, and their asymmetric Diels-Alder reactions with cyclopentadiene are studied. The reactions of (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone with cyclopentadiene, catalyzed by TiCl4, allow...
| Autores: | , , , , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 1992 |
| País: | España |
| Recursos: | Universidad de La Rioja (UR) |
| Repositorio: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc68fcb750603269e812ec |
| Acesso em linha: | https://investigacion.unirioja.es/documentos/5bbc68fcb750603269e812ec |
| Access Level: | acceso abierto |
| Resumo: | Several chiral derivatives of (E)-2-cyanocinnamic acid are used as trisubstituied dienophiles, and their asymmetric Diels-Alder reactions with cyclopentadiene are studied. The reactions of (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone with cyclopentadiene, catalyzed by TiCl4, allow the synthesis of enantiomerically pure cycloadducts whose absolute configurations are assigned by an X-ray diffraction study of enantiomerically pure (1S,2S,3R,4R,5R,6R)-iodolactone. The results obtained show that the α-cyano group influences asymmetric induction, probably through an influence on the s-cis/s-trans equilibrium of the enoate moiety of the chiral dienophile. © 1992 American Chemical Society. |
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