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

共 50 条

[21] Palladium-catalyzed asymmetric allylic alkylations using diphenylphosphino(oxazolinyl)ferrocene ligands: Effects of planar chirality on the reactivity and selectivity
Ahn, KH
Cho, CW
Park, J
Lee, S
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1997, 18 (08) : 789 - 791
[22] The role of nitrogen-donor ligands in the palladium-catalyzed polyketones synthesis
Durand, J
Milani, B
COORDINATION CHEMISTRY REVIEWS, 2006, 250 (3-4) : 542 - 560
[23] Novel and efficient chiral sulfideoxathiane ligands for palladium-catalyzed asymmetric allylic alkylation
Okuyama, Y
Nakano, H
Takahashi, K
Hongo, H
Kabuto, C
CHEMICAL COMMUNICATIONS, 2003, (04) : 524 - 525
[24] Development of Chiral Terminal-Alkene-Phosphine Hybrid Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions
Liu, Zhaoqun
Du, Haifeng
ORGANIC LETTERS, 2010, 12 (13) : 3054 - 3057
[25] C2-symmetric bis-thioglycosides as new ligands for palladium-catalyzed allylic substitutions
Khiar, N
Araújo, CS
Alvarez, E
Fernández, I
TETRAHEDRON LETTERS, 2003, 44 (16) : 3401 - 3404
[26] 1-phosphino-2-sulfenylferrocenes as planar chiral ligands in enantioselective palladium-catalyzed allylic substitutions
Mancheño, OG
Priego, J
Cabrera, S
Arrayás, RG
Llamas, T
Carretero, JC
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09): : 3679 - 3686
[27] PALLADIUM-CATALYZED TELOMERIZATION OF DIENES AND TERTIARY ALLYLIC AMINES - A NOVEL REACTION INVOLVING CLEAVAGE OF THE CARBON NITROGEN BOND
ANTONSSON, T
MOBERG, C
ORGANOMETALLICS, 1985, 4 (06) : 1083 - 1086
[28] Palladium-Catalyzed Aerobic Oxidative Coupling of Allylic Alcohols with Anilines in the Synthesis of Nitrogen Heterocycles
Kumar, Gangam Srikanth
Singh, Diksha
Kumar, Manish
Kapur, Manmohan
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 3941 - 3951
[29] Novel chiral phosphine-oxazinane ligands in palladium-catalyzed asymmetric allylic alkylation
Mino, T
Hata, S
Ohtaka, K
Sakamoto, M
Fujita, T
TETRAHEDRON LETTERS, 2001, 42 (29) : 4837 - 4839
[30] Chiral phenylselenyl derivatives of pyrrolidine and Cinchona alkaloids:: nitrogen-selenium donating ligands in palladium-catalyzed asymmetric allylic alkylation
Zielinska-Blajet, Mariola
Siedlecka, Renata
Skarzewski, Jacek
TETRAHEDRON-ASYMMETRY, 2007, 18 (01) : 131 - 136

← 1 2 3 4 5 →