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Asymmetric Hydrogenation of Aromatic, Aliphatic, and α,β‐Unsaturated Acyl Silanes Catalyzed by Tol‐binap/Pica Ruthenium(II) Complexes: Practical Synthesis of Optically Active α‐Hydroxysilanes
Author(s) -
Arai Noriyoshi,
Suzuki Ken,
Sugizaki Satoshi,
Sorimachi Hiroko,
Ohkuma Takeshi
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200704696
Subject(s) - silanes , allylic rearrangement , chemistry , optically active , catalysis , ruthenium , alkyl , organic chemistry , binap , enantioselective synthesis , aryl , medicinal chemistry , silane
A catalytic system of Ru II complex (see scheme; Ar=4‐CH 3 C 6 H 4 ; R=H, t ‐C 4 H 9 ) and t ‐C 4 H 9 OK or NaBH 4 activator has been used in the hydrogenation of aromatic and aliphatic acyl silanes to give α‐hydroxysilanes with high enantioselectivity (R 1 =aryl, alkyl, alkenyl; R 2 = t ‐C 4 H 9 , C 6 H 5 ). Optically active allylic α‐hydroxysilanes are obtained in the 1,2‐reduction of α,β‐unsaturated acyl silanes. These chiral α‐hydroxysilanes are converted into 4‐substituted 2‐cyclopentenones without loss of enantioselectivity.