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Ring Expansion – Formation of Optically Active 3‐Hydroxypiperidines from Pyrrolidinemethanol Derivatives
Author(s) -
Cossy Janine,
Dumas Cécile,
Pardo Domingo Gomez
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199907)1999:7<1693::aid-ejoc1693>3.0.co;2-j
Subject(s) - chemistry , trifluoroacetic anhydride , optically active , enantiomer , hydrolysis , ring (chemistry) , trifluoroacetic acid , enantiomeric excess , organic chemistry , medicinal chemistry , enantioselective synthesis , catalysis
Treatment of pyrrolidinemethanol derivatives (–)‐1 , (–)‐6 , (–)‐7 , 8 , (–)‐9 , (+)‐10 , (–)‐11 , and (–)‐21 with trifluoroacetic anhydride and then with Et 3 N 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 %).