Premium
Easily Accessible Chiral P,N ‐Bidentate Aryl Phosphites, Their Complexation and Application in Enantioselective Allylic Alkylation, Sulfonylation and Hydrosilylation
Author(s) -
Gavrilov Konstantin N.,
Bondarev Oleg G.,
Lebedev Roman V.,
Shiryaev Alexei A.,
Lyubimov Sergey E.,
Polosukhin Alexei I.,
GrintselevKnyazev Gennady V.,
Lyssenko Konstantin A.,
Moiseev Sergey K.,
Ikonnikov Nikolay S.,
Kalinin Valery N.,
Davankov Vladim A.,
Korostylev Andrei V.,
Gais HansJoachim
Publication year - 2002
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/1099-0682(200206)2002:6<1367::aid-ejic1367>3.0.co;2-f
Subject(s) - chemistry , hydrosilylation , medicinal chemistry , enantioselective synthesis , denticity , alkylation , aryl , acetophenone , chelation , tsuji–trost reaction , phosphine , dimethyl malonate , stereochemistry , organic chemistry , catalysis , alkyl , crystal structure
New chiral P , N ‐hybrid aryl phosphites have been obtained by one‐step phosphorylation of amino and imino alcohols. Complexation of the new ligands with [Rh(CO) 2 Cl] 2 , [Pd(COD)Cl 2 ] and [Pd(allyl)Cl] 2 was found to give chelate complexes [Rh(CO)Cl(η 2 ‐P ∩ N)], [PdCl 2 (η 2 ‐P ∩ N)] and [Pd(allyl)(η 2 ‐P ∩ N)] + Cl − , respectively. With these new P , N ‐ligands, up to 82% ee enantioselectivity was achieved in the Pd‐catalysed alkylation of ethyl 3‐penten‐2‐yl carbonate with dimethyl malonate, up to 80% ee in the Pd‐catalysed sulfonylation of methyl 3‐penten‐2‐yl carbonate with sodium p ‐toluenesulfinate, and up to 50% ee in the Rh‐catalysed hydrosilylation of acetophenone with diphenylsilane. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)