http://www.cnr.it/ontology/cnr/individuo/prodotto/ID178791
Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system (Articolo in rivista)
- Type
- Label
- Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system (Articolo in rivista) (literal)
- Anno
- 2006-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1016/j.tetasy.2006.11.041 (literal)
- Alternative label
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Laura Palombi; Maria Rosaria Acocella; Nicoletta Celenta; Antonio Massa; Rosaria Villano; Arrigo Scettri (literal)
- Pagina inizio
- Pagina fine
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
- Rivista
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
- Note
- Scopu (literal)
- ISI Web of Science (WOS) (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
- Dipartimento di Chimica, Universita` degli Studi, Via Ponte don Melillo, I-84084 Fisciano, Salerno, Italy (literal)
- Titolo
- Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system (literal)
- Abstract
- This paper reports the regio-, diastereo- and highly enantioselective vinylogous aldol reaction of 2-trimethylsilyloxyfuran (TMSOF) promoted by the SiCl4/Lewis base catalytic system. Several electron-pair donors proved to be effective as SiCl4 activators versus the TMSOF gamma-selective addition to aldehydes giving rise to different diastereoisomeric ratios, while Denmark's chiral bis-phosphoramide (R,R)-7 gave the highest enantioselectivity for both the anti- and syn-diastereoisomers. Furthermore, by using ambident electrophiles such as alpha,beta-unsaturated aldehydes, the SiCl4/Lewis base-promoted process leads exclusively to the 1,2-addition products. (literal)
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- Autore CNR
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