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Ring Expansion - Formation of Optically Active 3-Hydroxypiperidines from Pyrrolidinemethanol Derivatives (1999)

Cossy, Janine ; Dumas, Cécile ; Pardo, Domingo Gomez

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 1693-1699

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ISSN: 1434-193X

Keywords: Pyrrolidines ; Piperidines ; Nitrogen heterocycles ; Rearrangements ; Aziridinium ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Treatment of pyrrolidinemethanol derivatives (-)-1, (-)-6, (-)-7, 8, (-)-9, (+)-10, (-)-11, and (-)-21 with trifluoroacetic anhydride and then with Et3N afforded, after hydrolysis of the trifluoroacetyl group with NaOH, the optically active 3-hydroxypiperidines (-)-14, (+)-15, (-)-16, 17, (+)-18, (-)-19, (-)-20, and (+)-22, respectively. The yields are good and the enantiomeric excess excellent (up to 95 %).

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

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