Easily accessible chiral P,N-bidentate aryl phosphites, their complexation and application in enantioselective allylic alkylation, sulfonylation and hydrosilylation

Gavrilov, KN; Bondarev, OG; Lebedev, RV; Shiryaev, AA; Lyubimov, SE; Polosukhin, AI; Grintselev-Knyazev, GV; Lyssenko, KA; Moiseev, SK; Ikonnikov, NS; Kalinin, VN; Davankov, VA; Korostylev, AV; Gais, HJ

HERO ID

4936264

Reference Type

Journal Article

Year

2002

HERO ID 4936264
In Press No
Year 2002
Title Easily accessible chiral P,N-bidentate aryl phosphites, their complexation and application in enantioselective allylic alkylation, sulfonylation and hydrosilylation
Authors Gavrilov, KN; Bondarev, OG; Lebedev, RV; Shiryaev, AA; Lyubimov, SE; Polosukhin, AI; Grintselev-Knyazev, GV; Lyssenko, KA; Moiseev, SK; Ikonnikov, NS; Kalinin, VN; Davankov, VA; Korostylev, AV; Gais, HJ
Journal European Journal of Inorganic Chemistry
Issue 6
Page Numbers 1367-1376
Abstract 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(eta(2)-(PN)-N-boolean AND)], [PdCl2(eta(2)-(PN)-N-boolean AND)] and [Pd(allyl) (eta(2)-(PN)-N-boolean AND)]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. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
Wosid WOS:000175988500014
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Keyword aryl phosphites; N,P ligands; palladium; allylation; rhodium; hydrosilylation