Nitrogen-Based Chirality Effects in Novel Mixed Phosphorus/Nitrogen Ligands Applied to Palladium-Catalyzed Allylic Substitutions

被引：9

作者：

Schnitzler, Verena ^{[1
]}

Nonglaton, Guillaume ^{[1
]}

Roussiere, Helene ^{[1
]}

Maillet, Celine ^{[1
]}

Evain, Michel ^{[2
]}

Janvier, Pascal ^{[1
]}

Bujoli, Bruno ^{[1
]}

Petit, Marc ^{[1
]}

机构：

[1] Univ Nantes, CNRS, CEISAM, UFR Sci & Tech,UMR 6230, F-44322 Nantes 2, France

[2] Univ Nantes, CNRS, Inst Mat Jean Rouxel, UMR 6502, F-44322 Nantes 2, France

来源：

ORGANOMETALLICS | 2008年 / 27卷 / 22期

关键词：

D O I：

10.1021/om800498a

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A novel series of chiral P,N-ligands was obtained by desymmetrization of the achiral meso-N,N'-dimethyl-1,2-diphenylethane-1,2-diamine backbone and resolution of the resulting adducts. This transformation was achieved by the selective introduction of a diphenylphosphine moiety on one of the two nitrogen centers. The resulting palladium complexes were used for the catalytic enantioselective allylic alkylation of 1,3-diphenyl-1-acetoxy-2-propene with dimethyl malonate. In some cases, high conversions (up to 98% after 1 h) along with good chiral inductions (up to 95% e.e.) were obtained, as a result of a control of the inversion of the stereogenic center formed at nitrogen upon coordination to palladium.

引用

页码：5997 / 6004

页数：8

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