Premium
Properties and reactions of substituted 1,2‐thiazetidine 1,1‐dioxides: Acylation of β‐sultams at C‐4, reduction of 4‐acyl‐β‐sultams, and stereochemistry of 4‐(α‐hydroxyalkyl)‐β‐sultams
Author(s) -
Müller Martin,
Otto HansHartwig
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910131
Subject(s) - chemistry , sodium borohydride , acylation , diastereomer , stereochemistry , organic chemistry , catalysis
Acylation of N ‐silylated and 2,3‐substituted 1,2‐thiazetidine 1,1‐dioxides (β‐sultams) results in the formation of 4‐acylated β‐sultams 2 and 8 . The desilylation of 2 to 3 is easily done with TBAF either on silica gel or in ethanolic solution. The acylated β‐sultams are reduced by sodium borohydride yielding α‐hydroxyalkyl β‐sultams 11 and 12 , obtained as mixtures of diastereoisomers. These are separated by CC. The stereochemistry of the acylated and of the α‐hydroxylated β‐sultams is elucidated by spectroscopic methods, and compared to that of the antibiotic drug thienamycin.