✦ LIBER ✦

The addition of 2-tert-butyldimethylsilyloxyfuran to cyclic N-acyliminium ions containing cyclohexyl-based chiral auxiliaries

✍ Scribed by Marcelo G.M D'Oca; Ronaldo A Pilli; Ivo Vencato

Book ID: 104211296
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 75 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01749-4

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✦ Synopsis

The vinylogous Mannich addition of silyloxyfuran 5 to chiral five-and six-membered N-acyliminium ions derived from 3/4a,b occurred exclusively through the addition to the N-acyliminium Si face to provide threo-6/7a,b as the major isomer (73-84% yield, 2:1-7:1 diastereoisomeric ratio) which were converted to the corresponding bicyclic lactams 10 and 11 with efficient recovery of the chiral auxiliary.

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