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Enantioselective Intramolecular Reductive Heck Reaction with a Palladium/Monodentate Phosphoramidite Catalyst
Author(s) -
Mannathan Subramaniyan,
Raoufmoghaddam Saeed,
Reek Joost N. H.,
de Vries Johannes G.,
Minnaard Adriaan J.
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201601153
Subject(s) - phosphoramidite , palladium , chemistry , heck reaction , enantioselective synthesis , organic chemistry , catalysis , denticity , intramolecular force , diethyl carbonate , combinatorial chemistry , medicinal chemistry , ethylene carbonate , dna , biochemistry , oligonucleotide , crystal structure , electrode , electrolyte
A palladium‐catalyzed enantioselective reductive Heck reaction of enones using monodentate phosphoramidite ligands is described. α,α,α’,α’‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanol (TADDOL)‐based phosphoramidites with palladium(II) acetate, and N ‐methyl dicyclohexylamine as reducing agent gives the reductive Heck product in high yields and enantioselectivities of up to 90 %. The solvent plays an important role and in diethyl carbonate, the chemo‐ and enantioselectivity appeared to be the highest.