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N‐(α‐Chloroalkyloxycarbonyl)pyrrolidines as a Source of Oxygenated d 1 ‐Reagents
Author(s) -
Ortiz Javier,
Guijarro Albert,
Yus Miguel
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(199911)1999:11<3005::aid-ejoc3005>3.0.co;2-7
Subject(s) - chemistry , electrophile , hydrolysis , reagent , lithium (medication) , catalysis , hydroxide , organic chemistry , ethanol , lithium hydroxide , medicinal chemistry , medicine , ion , ion exchange , endocrinology
Reaction of the N ‐(α‐chloroalkyloxycarbonyl)pyrrolidines 1 with lithium powder and a catalytic amount of 4,4′‐di‐ tert‐ butylbiphenyl (DTBB, 2.5 mol‐%) in the presence of different electrophiles [ i BuCHO, t BuCHO, PhCHO, Et 2 CO, (CH 2 ) 5 CO, PhCOMe, Ph 2 CO, Me 3 SiCl], in THF at temperatures ranging between –78 and –60°C leads, after hydrolysis with water, to the expected functionalized carbamates 2 . Deprotection of compounds 2 , derived from carbonyl compounds, with lithium hydroxide in a mixture of ethanol and water at 80°C affords the correponding 1,2‐diols 3 .