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Pyridyl Phosphinites and Pyridyl Phosphites from Chiral Pyridyl Alcohols — A Modular Approach
Author(s) -
Rahm Fredrik,
Fischer Andreas,
Moberg Christina
Publication year - 2003
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.200300368
Subject(s) - chemistry , diethylzinc , kinetic resolution , benzaldehyde , malonate , dimethyl malonate , palladium , catalysis , organic chemistry , chirality (physics) , medicinal chemistry , enantioselective synthesis , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
Chiral arylated pyridyl alcohols, pyridyl phosphinites and pyridyl phosphites were prepared by Suzuki arylation and/or O ‐functionalization with a chlorodiarylphosphane or a chlorodiarylphosphite of chiral 2‐bromo‐6‐(1‐hydroxyalkyl)pyridines or 2‐(1‐hydroxyalkyl)pyridines, with the chirality originating from the chiral pool. The pyridyl alcohols were assessed as catalysts for the addition of diethylzinc to benzaldehyde and the P,N‐ligands were employed in the palladium‐catalysed substitutions of rac ‐1,3‐diphenyl‐2‐propenyl acetate and rac ‐2‐cyclohexenyl acetate with dimethyl malonate. Moderate enantioselectivities were observed in the catalytic reactions. We observed kinetic resolution of the racemic acetate when using one of the phosphite ligands. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)