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Modification of Chiral Monodentate Phosphine Ligands (MOP) for Palladium‐Catalyzed Asymmetric Hydrosilylation of Cyclic 1,3‐Dienes
Author(s) -
Hayashi Tamio,
Han Jin Wook,
Takeda Akira,
Tang Takeda,
Nohmi Kenji,
Mukaide Kotaro,
Tsuji Hayato,
Uozumi Yasuhiro
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(20010330)343:3<279::aid-adsc279>3.0.co;2-5
Subject(s) - chemistry , trichlorosilane , hydrosilylation , cyclopentadiene , palladium , phosphine , cyclopentene , aryl , medicinal chemistry , denticity , catalysis , enantioselective synthesis , stereochemistry , organic chemistry , crystal structure , alkyl , silicon
Several MOP ligands 5 containing aryl groups at 2′ position of ( R )‐2‐(diphenylphosphino)‐1,1′‐binaphthyl skeleton were prepared and used for palladium‐catalyzed asymmetric hydrosilylation of cyclic 1,3‐dienes 6 with trichlorosilane. Highest enantioselectivity was observed in the reaction of 1,3‐cyclopentadiene ( 6a ) catalyzed by a palladium complex (0.25 mol %) coordinated with ( R )‐2‐(diphenylphosphino)‐2′‐(3,5‐dimethyl‐4‐methoxyphenyl)‐1,1′‐binaphthyl ( 5f ), which gave ( S )‐3‐(trichlorosilyl)cyclopentene of 90% ee.