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Monodeazacinchona Alkaloid Derivatives: Synthesis and Preliminary Applications as Phase‐Transfer Catalysts
Author(s) -
Dehmlow Eckehard Volker,
Düttmann Stephanie,
Neumann Beate,
Stammler HansGeorg
Publication year - 2002
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 - 10.1002/1099-0690(200207)2002:13<2087::aid-ejoc2087>3.0.co;2-z
Subject(s) - chemistry , cinchona , quinoline , catalysis , cinchona alkaloids , nitrogen atom , alkaloid , organic chemistry , natural product , phase (matter) , combinatorial chemistry , enantioselective synthesis , group (periodic table)
Four analogues of cinchona alkaloids ( 5 − 8 ) lacking the quinoline nitrogen atom have been prepared. Quaternization afforded the phase‐transfer catalysts 10a , 10b , 11a , and 12d . Other optically active catalyst salts were prepared from the cinchona alkaloids themselves (compounds 13 , 14 , 15 ). The performances of these PT catalysts and of some others were compared in three test reactions. The deazacinchona derivatives exhibited selectivities similar to or sometimes even better than those of the natural product‐derived compounds. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)