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Highly Diastereoselective Synthesis of 2,6‐Di[1‐(2‐alkylaziridin‐1‐yl)alkyl]pyridines, Useful Ligands in Palladium‐Catalyzed Asymmetric Allylic Alkylation
Author(s) -
Savoia Diego,
Alvaro Giuseppe,
Di Fabio Romano,
Fiorelli Claudio,
Gualandi Andrea,
Monari Magda,
Piccinelli Fabio
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606109
Subject(s) - chemistry , enantiopure drug , palladium , dimethyl malonate , carbanion , alkyl , tsuji–trost reaction , alkylation , medicinal chemistry , catalysis , enantiomer , yield (engineering) , malonate , enantiomeric excess , enantioselective synthesis , organic chemistry , stereochemistry , materials science , metallurgy
C 2 ‐Symmetrical, enantiopure 2,6‐di[1‐(1‐aziridinyl)alkyl]pyridines (DIAZAPs) were prepared by a high‐yielding, three‐step sequence starting from 2,6‐pyridinedicarbaldehyde and ( S )‐valinol or ( S )‐phenylglycinol. The new compounds were tested as ligands in palladium‐catalyzed allylation of carbanions in different solvents. Almost quantitative yield and up to 99 % enantiomeric excess were obtained in the reactions of the enolates derived from malonate, phenyl‐ and benzylmalonate dimethyl esters with 1,3‐diphenyl‐2‐propenyl ethyl carbonate.