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Ring Expansion – Formation of Optically Active 3-Hydroxypiperidines from Pyrrolidinemethanol Derivatives

✍ Scribed by Janine Cossy; Cécile Dumas; Domingo Gomez Pardo

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 291 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199907)1999:7<1693::aid-ejoc1693>3.0.co;2-j

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✦ Synopsis

Treatment of pyrrolidinemethanol derivatives (-)-1, (-)-6, (-)-3-hydroxypiperidines (-)-14, (+)-15, (-)-16, 17, (+)-18, (-)-19, (-)-20, and (+)-22, respectively. The yields are good and the 7, 8, (-)-9, (+)-10, (-)-11, and (-)-21 with trifluoroacetic anhydride and then with Et 3 N afforded, after hydrolysis of enantiomeric excess excellent (up to 95 %). the trifluoroacetyl group with NaOH, the optically active reverse reaction C Ǟ B Ǟ A is also possible. Because of In contrast with this reaction course, treatment of (؊)-1,

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