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Pyridinium Ions Adjacent to Oxirane Rings: Useful Intermediates for the Stereospecific Synthesis of β‐Hydroxy Ketones
Author(s) -
AlAbed Yousef,
Naz Noshena,
Khan Khalid Mohammed,
Voelter Wolfgang
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199605231
Subject(s) - pyridinium , stereospecificity , chemistry , pyridine , hydrolysis , ring (chemistry) , ion , organic chemistry , medicinal chemistry , catalysis
α,β‐Epoxytriflates like epoxytriflate pyranoside 1 undergo rearrangement in a one‐pot reaction after treatment with pyridine. The epoxy ring is opened giving N ‐vinylpyridinium derivatives such as 2 , which can be reduced with NaBH 4 and hydrolyzed under acidic conditions to give β‐hydroxy ketones. This generally applicable procedure can be used to convert easily accessible epoxypyranoses into deoxyketo sugars like 3 in high yields.