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The asymmetric synthesis of ( R,R )‐formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water
Author(s) -
Huang Ling,
Liu Juntao,
Shan Wenjun,
Liu Bao,
Shi Anding,
Li Xingshu
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.20728
Subject(s) - chemistry , transfer hydrogenation , acetophenone , catalysis , sodium formate , nitro , polyethylene glycol , tppts , alcohol , phenylacetylene , asymmetric hydrogenation , ligand (biochemistry) , peg ratio , medicinal chemistry , formoterol , organic chemistry , polymer chemistry , hydroformylation , enantioselective synthesis , ruthenium , medicine , biochemistry , alkyl , receptor , rhodium , budesonide , inhalation , anatomy , finance , economics
( R,R )‐formoterol was synthesized in seven steps with 4‐hydroxyl‐3‐nitro‐acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4 , was prepared via Rh‐catalyzed asymmetric transfer hydrogenation with ( S,S )‐PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild conditions. With a mixture of PEG 2000 and water as the reaction media, the catalyst system could be recycled four times. Chirality, 2010. © 2009 Wiley‐Liss, Inc.