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Concave Pyridines for Selective Acylations of Polyols
Author(s) -
Lüning Ulrich,
Petersen Sönke,
Schyja Wolfgang,
Hacker Wolfgang,
Marquardt Torsten,
Wagner Kerstin,
Bolte Michael
Publication year - 1998
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(199806)1998:6<1077::aid-ejoc1077>3.0.co;2-6
Subject(s) - chemistry , acylation , selectivity , catalysis , ring (chemistry) , glucoside , base (topology) , stereochemistry , organic chemistry , medicinal chemistry , medicine , mathematical analysis , alternative medicine , mathematics , pathology
Selectivity enhancements in the base‐catalyzed acylation of polyols (1,2‐ or 1,3‐alkanediol, partially protected glucoside) have been found with (bi)macrocyclic pyridines 2 and 9 as catalysts. The different selectivities obtained for concave pyridines of varying ring sizes ( 1 vs. 2 ) are probably caused by their different geometries as a number of X‐ray analyses ( 1a , 1b , 2a , 2b , 2e , 9 ) indicate. The methyl glucoside 7 can selectively be acylated in 2‐position.