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( S )‐6‐Bromo‐BINOL‐based phosphoramidite ligand with C 1 symmetry for enantioselective hydrogenation and allylic substitution
Author(s) -
Gavrilov Konstantin N.,
Benetsky Eduard B.,
Boyko Vladimir E.,
Rastorguev Eugenie A.,
Davankov Vadim A.,
Schäffner Benjamin,
Börner Armin
Publication year - 2010
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20845
Subject(s) - allylic rearrangement , chemistry , phosphoramidite , enantioselective synthesis , stereocenter , amination , tsuji–trost reaction , ligand (biochemistry) , medicinal chemistry , chirality (physics) , substitution reaction , palladium , catalysis , denticity , stereochemistry , organic chemistry , crystal structure , symmetry breaking , dna , biochemistry , chiral symmetry breaking , receptor , physics , quantum mechanics , nambu–jona lasinio model , oligonucleotide
( S )‐6‐Br‐BINOL‐derived phosphoramidite, a s imple monodentate ligand with a stereogenic center at the phosphorus atom, was synthesized for the first time. This stereoselector generated a high level of enantioselectivity (80–95% ee ) in the rhodium‐catalyzed hydrogenation of α‐dehydrocarboxylic acid esters and was also successfully employed in the asymmetric palladium‐catalyzed allylic substitution of ( E )‐1,3‐diphenylallyl acetate. The optical yield also showed significant dependence with reaction type: up to 70% ee for allylic amination, up to 75% ee for allylic sulfonylation, and up to 90% ee for allylic alkylation. Chirality, 2010. © 2010 Wiley‐Liss, Inc.
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