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First Generation Cysteine‐ and Methionine‐Derived Oxazolidine and Thiazolidine Ligands for Palladium‐Catalyzed Asymmetric Allylations
Author(s) -
Schneider Paulo H.,
Schrekker Henri S.,
Silveira Claudio C.,
Wessjohann Ludger A.,
Braga Antonio L.
Publication year - 2004
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/ejoc.200300675
Subject(s) - chemistry , thiazolidine , oxazolidine , enantiopure drug , palladium , thioether , aldol reaction , dimethyl malonate , yield (engineering) , catalysis , organic chemistry , enantiomer , cysteine , enantioselective synthesis , medicinal chemistry , enzyme , materials science , metallurgy
A new series of enantiopure oxazolidine‐thioether and thiazolidine‐alcohol ligands have been synthesized from L ‐cysteine, S ‐methyl‐ L ‐cysteine, and L ‐methionine in a straightforward manner that allows numerous structural variations to be formed. These types of ligands have not previously been used in asymmetric palladium‐catalyzed allylations and their efficacy was explored in the reaction of rac ‐1,3‐diphenyl‐2‐propenyl acetate with dimethyl malonate. The reaction proceeds in excellent yield and with good enantioselectivity. The palladium catalyst derived from N ‐benzyl‐2,2‐dimethyl‐4‐(2‐thiapropyl)oxazolidine ( 12 ) provides the allylation product in a quantitative yield and with an enantiomeric excess of 94%. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)